Car Thread - Most Mustachian Car in my situation

[cbr shadow]

I'm going to be buying a car in Chicago and driving it from Chicago to San Francisco pulling a small Uhaul trailer.  Then my wife and I will likely share the car in SF (Her occasional commute, me for general use and for transporting our dogs around). I plan on buying used, probably from Craigslist.  I've bought/sold many cars on Craigslist in the past.  What car model/year would best fit my situation?  Here are the criteria

1) Has to be able to pull a small U-Haul trailer across the country - Most compact cars can do this, but I believe the Prius is not rated for any towing
2) Automatic Transmission
3) 4 Doors
4) Good reputation for reliability

$13k maximum spend, although I'd like to make it less if possible.

So far I've considered:
2008-2011 Honda Civic
2010-12 Toyota Corolla (Although wife thinks these are less professional looking than the Civic.  Not sure why she thinks that.  Generally they do cost a bit less!)
2008-2010 Toyota Matrix
2009-2011 Nissan Sentra
2009-2011 Nissan Versa
2009-2012 Kia Forte
2009-2012 Hyundai Elantra

Those are probably the most mustachian cars I'm looking at.  Any other suggestions?

I've also looked a bit at two luxury vehicles that "would be nice" to have, but cost a bit more than the above.
2007-2009 Lexus IS250
2006-2009 Lexus RX350
I've driven both of these before and liked how quiet they were compared to the economy cars above, and Lexus has an outstanding reputation for reliability.  These would require more money up front though, and the RX350 gets 24mpg compared to 30's for all of the above cars.

Any models I should look at?

Thanks,
CBR

Edit:  Worth mentioning, I know the Honda Fit will come up as a suggestion.  While I do like the Honda Fit for it's "magic seats", I find they're a bit loud while driving on the highway.  On top of that compaint, they generally sell for more than most of the other cars I've listed (including the Civic) which is odd to me.

[horsepoor]

Mazda 3 and either of the Scions would be worth considering too.  I think the SkyActiv on the Mazda became available in '12; imagine you could find one of that year for under $13K.  With that one you have the option of sedan or hatch, depending on your preference.

Hard to go wrong with a Civic or Corolla.

[cbr shadow]

Thanks for the suggestions about the Scions.  I looked into those a bit, but I think the XD is the only one that will work for us.  I had a 2006 XB in the past (the boxy model) and loved it, but wife didn't like the looks.  The newer model seems to have gotten rid of all of the best features.. Newer XB gets poor gas mileage and much less storage space.  I guess they're cooler looking and have a bit more power, but c'mon Function over Fashion :)

The XD is worth considering though - I'll take a look at that.
I hadn't heard of Skyactiv before.  I am a bit biased against Mazda because a friend had a real lemon, but I should get over that.

[alsoknownasDean]

Are the hatchback versions of the Kia and Hyundai available in your market? Modern day Kia and Hyundai cars are reliable and pretty cheap second hand.

Otherwise, the Honda/Toyota/Nissan/Mazda/Mitsubishi/etc should all be fine if you get a good well maintained example.

The Ford Focus or Chevy Cruze might be worth considering too, especially if they're cheaper than the Japanese vehicles.

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[captainawesome]

If you are willing to expand a little bit, in 13 Kia and Hyundai updated their hatchback line up in the Forte and Elantra GT respectively.  You can get pretty good prices on those pre-owned.  I have a 14 Elantra GT and it is great, and I bought it pre-owned with 13k miles for 15k fully loaded (leather, sunroof, nav etc). I didn't need any of the extras, but the dealership selling it didnt really price it differently than a similar model without.

My wife drives a Mazda, and my previous car was a mazda. They are great. Hers actually gets better gas mileage than my car. 

In my pre mustachian life I owned an IS250 AWD. It was nice, but noticeably cramped interior, and not great backseat room for any passengers. Also, Lexus models take premium fuel.  If you are considering a Lexus for any reason, look at a pre-owned ct200H.  I've seen 2012's going from 12-15k.  Same as a Prius in terms of drive train, just looks better IMO (and doesn't take premium fuel).

[going2ER]

I don't know alot about cars so take it for what it is worth. My husband worked for a Honda dealership in the past and says you shouldn't haul anything with them and that is why they don't come with anywhere to put a trailer hitch, so something to check out.

I have a Mazada 3 and can not say enough good things about it. It has lots of power and takes very little gas. I have never towed anything with it so I can't comment on that aspect of it.

[HipGnosis]

What are you going to put in the trailer?
The UHaul 4x8 empty weight is: 850 lbs.  Max load is: 1,650 lbs., which means you could be towing  2,500 lbs!   That's more than a compact car can handle.
Call UHaul at 800-468-4285 for specific info.
And read:  https://rideapart.com/articles/top-five-small-and-inexpensive-cars-that-can-towhaul

[lbmustache]

What are you going to put in the trailer?
The UHaul 4x8 empty weight is: 850 lbs.  Max load is: 1,650 lbs., which means you could be towing  2,500 lbs!   That's more than a compact car can handle.
Call UHaul at 800-468-4285 for specific info.
And read:  https://rideapart.com/articles/top-five-small-and-inexpensive-cars-that-can-towhaul

I thought the weight was calculated as part of the max load. Which means OP can tow about ~800lbs on top of the weight of the 4x8? So a tow rating of 2000b on most of these cars should be ok?

[CanuckExpat]

I'm wondering about your towing situation and what made you decide to go this route, more out of curiosity then criticism.

Do the smaller compact cars have 1 1/4" or 2" hitch receivers? My guess would be the former, and can you tow a U-Haul trailer that you want with that size?

Is automatic transmission a must-have? If I was doing a lot of towing and encountering hills, I think I'd feel more comfortable with a manual and would worry about overheating an automatic transmission (or have automatic transmissions improved past this being a concern?).

If the towing across the country is a one time deal, is another option to rent a U-Haul truck to move your stuff and then buy a car at your leisure in your final destination? Otherwise, could you buy your ideal commuter car and then tow that behind a truck? What are the financial costs of renting the trailer vs. renting a truck?

If towing with the compact works out well cost and practicality wise, let us know. I am very curious!

[use2betrix]

Some cars are rated for 1500 lbs. I'd look and make sure. You'll likely need a v6 unless it's a car with a turbo 4.

I have a 1999 Camry with a v6 and it's rated for 1500 lbs, and we have a hitch.

On a one time use, it may be worth getting a driving uhaul and towing the car or driving separate, unless the vehicle you get happens to be able to tow. I wouldn't make vast changes in your decision for a one time tow. If you plan to toe reasonably more, that's a different situation.

[sailinlight]

Have you priced out the cost to rent a small u-haul truck and then buy a car later?

[cbr shadow]

Thanks for the feedback so far.  All good points!  One reason I posted this question here was because I know Mustachians will question all aspects of my plans, which I appreciate!
Since this is a 1-way trip to SF, renting a U-haul truck/van would be extremely expensive ($2000 for the truck, $1700 for the van) where the small Uhaul trailer is $500. 
The other issue with renting a truck is that the box truck has only 2 seats, but I plan on driving with my wife and two dogs.  At least with a car the dogs can be in the back seat rather than in a dark box truck.  The cargo van would work, but is just too expensive.

So I figured my options are:

A) Rent a U-Haul Truck (~$2000), put dogs in rear area in their crates. Buy car in SF.  This is the worst option because of the dogs and because of the price.  Also I dont have enough stuff to justify using a box truck.

B) Rent a cargo van from Uhaul ($1700)  Buy car in SF. This is a reasonable option but still too expensive IMO.

C) Buy a car in Chicago, Rent Uhaul Trailer ($500).  Everything we're bringing will fit into a small trailer (4'x8').  Dogs can ride in the backseat.  The other upside is that when we get to SF we wont be in a massive rush to buy a car since we'll already have one.

D) Buy a cargo van from Craigslist in Chicago, Use the van to move and then resell it in SF.  This would be more trouble than it's worth because of registration/insurance/plates, plus I'd have to buy another car in SF.

E) Buy a car in Chicago, don't move any items to SF besides what will fit in the car (sell those items in Chicago).  Buy new/used items in SF.


I'm leaning towards options C or E. 

[Paul der Krake]

Will you be taking advantage of the moving expenses deduction? That may tilt the balance in favor of renting a truck.

[cbr shadow]

Most compact cars (like Toyota Corolla 4 cyl) are rated for 1500 lbs.  I believe the transmission is the bottleneck (overheating), not the engine being 4 cyl.

As for needing an Automatic over Manual, I'm told in SF a manual car is a PITA with the hills and traffic.  I much prefer the convenience of an automatic car anyway.  We do have a manual car right now and it's fine, but my wife's #1 request is that the next car is automatic.

[cbr shadow]

Good point on the moving expenses deduction - I'm going to look into this since I'm not familiar.
My wife's company is paying $5k in moving expenses, but without making this into a long/boring story these funds are eaten up by our move from Melbourne Australia to Chicago.

[ketchup]

Do keep in mind that a car you buy in SF will have essentially no rust compared to a Chicago car.  Rust kills cars and makes them look crappy.

Also, from the sounds of things you won't be towing much (any?) with the car after getting to SF, so making a decision with that being a big part of it may be a long-term solution to a short-term problem.  You may end up paying a premium (up-front or in operating costs) for a single-use that meets or exceeds the U-haul truck/van rental cost.

[alsoknownasDean]

Do keep in mind that a car you buy in SF will have essentially no rust compared to a Chicago car.  Rust kills cars and makes them look crappy.

Also, from the sounds of things you won't be towing much (any?) with the car after getting to SF, so making a decision with that being a big part of it may be a long-term solution to a short-term problem.  You may end up paying a premium (up-front or in operating costs) for a single-use that meets or exceeds the U-haul truck/van rental cost.

This.

Also, what are the costs of registering an out of state car in California? Does Illinois have the same regulations as CA?

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[Venturing]

Or another option
Buy a 'towing' car in Chicago. And drive it to cal.
Sell towing car in cal, it's job is done
Buy a small compact run around car in cal.

If you buy smart you could make a profit on the car that you buy and then sell.

In my experience it is rarely worth transporting stuff from one city to another. I'd be tempted to just take what fits in the car itself. With some smart buying you should be able to sell your stuff in Chicago and repurchase it in cal for the same or less money. That way you can also buy things that are the right size etc for your new house.

[cbr shadow]

Do keep in mind that a car you buy in SF will have essentially no rust compared to a Chicago car.  Rust kills cars and makes them look crappy.

Also, from the sounds of things you won't be towing much (any?) with the car after getting to SF, so making a decision with that being a big part of it may be a long-term solution to a short-term problem.  You may end up paying a premium (up-front or in operating costs) for a single-use that meets or exceeds the U-haul truck/van rental cost.

This.

Also, what are the costs of registering an out of state car in California? Does Illinois have the same regulations as CA?

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IMO the rust concern is grossly overstated.  I've always had 5-10 y.o. used cars in Chicago and none of them had any visible rust.  Lots of my friends drive older cars as well, and none of their cars have rust either.

Or another option
Buy a 'towing' car in Chicago. And drive it to cal.
Sell towing car in cal, it's job is done
Buy a small compact run around car in cal.

If you buy smart you could make a profit on the car that you buy and then sell.

In my experience it is rarely worth transporting stuff from one city to another. I'd be tempted to just take what fits in the car itself. With some smart buying you should be able to sell your stuff in Chicago and repurchase it in cal for the same or less money. That way you can also buy things that are the right size etc for your new house.

This option was considered, but I think it would be difficult to 'break even or profit' with the registration costs.  Also that would mean buying/selling twice instead of once, with the advantage being a more capable trailer towing car.  Most of the compact cars that I listed have 1500 lb towing capacity which is very much within what I will require.

I agree with the points about selling everything and buying again in SF though.. It'll take some time to sell everything, but would be nice to not have to deal w/ the Uhaul trailer!

[SeaEhm]

Honda Element.

Very versatile.  They stopped making them so depreciation should be very minimal.

Dogs?  The floor is plastic so messes clean up easily.

[galliver]

Do your prices include gas? Because in my calculations that was an extra $1k on the trucks...and would probably trash a car's MPG, especially if you were pushing its capabilities.

When my bf and I moved from IL to SoCal (LA area) 1.5 years ago, we found the best (cheapest/least hassle/least risk) way to move was to put our stuff in a UHaul U-Box (~$1k for 1 5'x8'x?? crate) and fly, then buy a car on this end. The tradeoffs would have been different if we'd had a car already though (my colleague did the roadtrip...but also sent stuff via U-Box). We also had no pets. You can also look into shipping stuff by Amtrak; I think you have to call or go to a train station and ask, they don't have a lot of info online, but it can be economical for smaller loads (it was our backup plan in case we had a few large boxes left or something).

If you don't like/trust UHaul or their boxes there are other services where you pack and they deliver, either into a pod/crate or into a truck (PODS, U-pack, etc...we had a good friend recommendation for DoorToDoor but they didn't work for us geographically, they do operate in Chicago though!) I would give the pod/crate/box form of moving a 4.5/5 for price and convenience. I would give our Uhaul experience specifically  more like 3/5: the franchise at our origin was awful, I wished they had a tracking system, but the experience/service on the LA end was great and redeemed them. Basically, shop around and read reviews, but if UBox is tantalizingly cheap, you can go with them and MOST likely be fine (take valuables with you...), just give yourself buffer time if possible in case your case is mishandled.

Even if you have to buy or rent a car in Chicago to get yourselves and the dogs to SF, you would get rid of the towing requirement and could go with something more compact (maybe even cheaper?) without risking being unable to make it up the Rockies!

[FINate]

Do your prices include gas? Because in my calculations that was an extra $1k on the trucks...and would probably trash a car's MPG, especially if you were pushing its capabilities.

When my bf and I moved from IL to SoCal (LA area) 1.5 years ago, we found the best (cheapest/least hassle/least risk) way to move was to put our stuff in a UHaul U-Box (~$1k for 1 5'x8'x?? crate) and fly, then buy a car on this end. The tradeoffs would have been different if we'd had a car already though (my colleague did the roadtrip...but also sent stuff via U-Box). We also had no pets. You can also look into shipping stuff by Amtrak; I think you have to call or go to a train station and ask, they don't have a lot of info online, but it can be economical for smaller loads (it was our backup plan in case we had a few large boxes left or something).

If you don't like/trust UHaul or their boxes there are other services where you pack and they deliver, either into a pod/crate or into a truck (PODS, U-pack, etc...we had a good friend recommendation for DoorToDoor but they didn't work for us geographically, they do operate in Chicago though!) I would give the pod/crate/box form of moving a 4.5/5 for price and convenience. I would give our Uhaul experience specifically  more like 3/5: the franchise at our origin was awful, I wished they had a tracking system, but the experience/service on the LA end was great and redeemed them. Basically, shop around and read reviews, but if UBox is tantalizingly cheap, you can go with them and MOST likely be fine (take valuables with you...), just give yourself buffer time if possible in case your case is mishandled.

Even if you have to buy or rent a car in Chicago to get yourselves and the dogs to SF, you would get rid of the towing requirement and could go with something more compact (maybe even cheaper?) without risking being unable to make it up the Rockies!

+1  Towing a trailer can easily cut MPG in half (depending on weight, aerodynamics). The UBox (or something similar) and then driving an efficient car or flying would be my choice.

One more point, parking in SF is a pain and almost all on-street, which means cars get beat up pretty badly. Not sure how it compares to Chicago (maybe all big cities are like this?). Just don't pay a premium for a newish car without exterior damage. Get something already beat up a bit. 

[marblejane]

On a side note, I split a UHaul truck rental with a friend to drive out from Chicago to SF. It was a 2 person cab in front, but there is a large space between the seats in the middle, where I threw down a dog bed and my dog happily chilled there the whole 4 days. So, it's certainly possible to just rent a small truck and have you two + dogs in the cab.

[couponvan]

Two suggestions.

1) Buy a Honda minivan and sell in CA. No uhaul, better gas mileage. I have a 2005 from CA originally that I am in IL with. Note that CA has different smog requirements for cars than IL-it could be expensive to move the car there and get it registered or sold.

2) Look at Broadway Express out of Effingham IL www.broadwayexpress.net (not .com) for shipping your stuff on a shared truck. U pack, U loaf, they drive, U unload. Get a quote.... I am completely serious when I tell you I have referred and successfully had FIVE different moves with friends through them. Me to IL 10 years ago full semi truck $6K. In laws to IL full semi truck $5.75K 8 years ago. Friend to IL from CA 7 years ago - partial truck, $1K (then back to CA w/ a new hub $1.5K partial truck). Just last Summer, our neighbors moved IL to CA full truck for $5.75K. With Spirit/Frontier Tuesday/Wednesday flights at $99 one way why drive and pay hotels unless you like road trips? I accept $100 gift cards if you like this option later. ;-) if you are flexible on leave dates you might get a better deal with them.

Normally I would be jealous of someone moving to CA in the Winter, but this winter has been so good.

[Urchina]

Subaru Outback?

And +1 on getting a vehicle that can pass smog in California. I don't know how the emissions standards here compare to those in other states, but it's something to be aware of.

[ketchup]

Do keep in mind that a car you buy in SF will have essentially no rust compared to a Chicago car.  Rust kills cars and makes them look crappy.

Also, from the sounds of things you won't be towing much (any?) with the car after getting to SF, so making a decision with that being a big part of it may be a long-term solution to a short-term problem.  You may end up paying a premium (up-front or in operating costs) for a single-use that meets or exceeds the U-haul truck/van rental cost.

This.

Also, what are the costs of registering an out of state car in California? Does Illinois have the same regulations as CA?

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IMO the rust concern is grossly overstated.  I've always had 5-10 y.o. used cars in Chicago and none of them had any visible rust.  Lots of my friends drive older cars as well, and none of their cars have rust either.

  Looking at just 5-10 year old cars seems short-sighted.  I live in the Chicago area and my cars are 15-24 years old and definitely have rust.  My dad drove his otherwise-perfectly-functional car to the junkyard last year because it was rusted out and unsafe to drive.  Rust spreads once it's there, and even if not visible, a 5-10 year old car in Chicago will have some.

[CanuckExpat]

As for needing an Automatic over Manual, I'm told in SF a manual car is a PITA with the hills and traffic.  I much prefer the convenience of an automatic car anyway.  We do have a manual car right now and it's fine, but my wife's #1 request is that the next car is automatic.

This concern is specific to living to living in the city of San Francisco, and also getting stuck doing a lot of stop and go traffic.
If you end up in the South Bay or Peninsula I think a manual or automatic would be fine, probably the same in the East Bay, but I've spent less time there to comment.

Either would be fine, except perhaps the overheating while towing problem; I think about finding a teardrop trailer to play with for camping, but the automatic makes me hesistant, though I'm sure it would be fine if you are careful.

The other obvious thing is to make sure you try the manual and automatic versions of the car you are trying. We have a Honda Fit with an automatic, it's a fine little car but I think it would be better with a manual. It's a small car with a small engine, the inefficiency and sluggishness of the automatic are visible at times, whereas in a car with a bigger engine the inefficiency of the transmission would be hidden by the extra power (a different kind of inefficiency).
We have the sport model which lets you select your gear even with the automatic, this is kind of nice on hilly highway driving, because I find the automatic is not very smart about getting into the right gear all the time. The automatic is also just a bit boring compared to a manual, but these are all concerns about non-traffic, non-stop-and-go, non-city-driving .. in a city with a lot of hills, I could see it being different.

[chris5977]

Have you considered going pet free? It sounds like these dogs are dictating how you live your life to a great degree, including the need to buy a car. Also it will be extremely difficult to find a pet friendly rental for two dogs. http://www.mrmoneymustache.com/2015/09/07/great-news-dog-ownership-is-optional/

[cbr shadow]

Wow lots of really good suggestions here.  Thanks for the efforts!

I'm reviewing the things we want to bring, and to be honest most of it means very little to us or is cheap furniture that can be very easily replaced.  I'm now considering selling everything in Chicago except what will fit in the car (and on a car-top carrier or trailer hitch rack) and then buying what we need on the CA side through Craigslist.  I think this may be the best way to go.

So back to square one.. What car models to look at?  The models I've listed above are still on the list, plus the suggestions you've given (Mazda3, Honda Element, Kia Forte, Hyundai Elantra, Ford/Chevy models on discount).

[cbr shadow]

Have you considered going pet free? It sounds like these dogs are dictating how you live your life to a great degree, including the need to buy a car. Also it will be extremely difficult to find a pet friendly rental for two dogs. http://www.mrmoneymustache.com/2015/09/07/great-news-dog-ownership-is-optional/

Chris, I can't tell if you're just trolling here or not.. could you be more specific about how we should go about doing this?  We're not killing our dogs in order to save some living expenses if that's what you're saying.  We chose to have dogs rather than kids (which are optional as well).
Have you considered going kid free?  Things would be much less expensive that way. 

Before moving to Melbourne I was told that we would never find a rental home that allows dogs, but we ended up with a wide selection of options.  We're in a similar situation with places in SF - my wife has called a few "pet friendly" rentals.

[chris5977]

Why would you think I was trolling? I linked the MMM blog post discussing how pet ownership is socially and financially irresponsible. But if your dogs make you happy, maybe it's worth it to you. Many pet owners get no joy from their animals. They got them because society expects you to own pets (and have a fancy car, and have 2.5 kids, and go to Disneyland, etc.) but to them they are just another responsibility. It sounds like you love your dogs. But if you don't enjoy your dogs perhaps you could give them to someone who does? Or kill them if you want to be dramatic.

I don't understand why you mentioned Melbourne because you said you were coming from Chicago. Are you talking about Melbourne Florida or Australia?

Being a Mustachian is more than simply buying a sensible car. It is a Way of Life. It would be helpful is you let the smart people here know exactly what is going on here. Where is your new job? Where is your wife's new job? Are you intent on moving to the City of San Francisco or the Bay Area?

[cbr shadow]

Why would you think I was trolling? I linked the MMM blog post discussing how pet ownership is socially and financially irresponsible. But if your dogs make you happy, maybe it's worth it to you. Many pet owners get no joy from their animals. They got them because society expects you to own pets (and have a fancy car, and have 2.5 kids, and go to Disneyland, etc.) but to them they are just another responsibility. It sounds like you love your dogs. But if you don't enjoy your dogs perhaps you could give them to someone who does? Or kill them if you want to be dramatic.

I don't understand why you mentioned Melbourne because you said you were coming from Chicago. Are you talking about Melbourne Florida or Australia?

Being a Mustachian is more than simply buying a sensible car. It is a Way of Life. It would be helpful is you let the smart people here know exactly what is going on here. Where is your new job. Where is your wife's new job. Are you intent on moving to the City of San Francisco or the Bay Area?

Chris,
I thought you were trolling because you had 1 forum post at the time (typical of trolls) , and you asked someone with 2 dogs if we've "considered going dog free".  It just seemed odd.  We do love our dogs and aren't getting rid of them.  We also have high incomes and a high savings rate, so I'm not sure anyone would describe us as financially irresponsible.  I also think being Mustachian is about optimizing happiness rather than just saving everywhere on expenses.. meaning "do my dogs bring $200/month worth of happiness".  In this case we've decided that they do.

I brought up Melbourne (Australia) because, as mentioned above,  that's where we currently live but will be moving back to Chicago (where we're originally from) before heading to the Bay Area.  When moving to Melbourne we were given the same warnings about how nobody would allow 2 big dogs in a rental but we found that this just wasn't the case.  The Bay Area so far has been similar but I guess we'll find out when my wife starts actually seeing the places in person.

So back to the car topic..
I do think the best option is going to be buying an inexpensive compact reliable car and driving to the Bay Area with whatever we can fit (without a trailer) and purchasing what's needed when we get to California.  The main thing I'll miss is our nice bed, which I wont be able to sell for much in Chicago and will need to buy new in California (Wife definitely won't go for a used bed) which, depending on what we go for can be pretty expensive.  Here in Australia we knew we would only be here for 2 years so we bought a bed setup from IKEA that has worked out well so far.  For longer-term use I'd probably want a regular mattress though.




 

[eljay]

Why are you making two long-distance moves in what sounds like a short time? Sounds hard on you and the dogs.

Can't you ship stuff + dogs Melbourne to SF direct, find rental, buy car and get settled. Then people get plane to Chicago at a later date while dogs stay in kennels.
OR
Leave dogs with friends in Melbourne until you've been to Chicago and are ready for them in SF

[chemistk]

So back to the car topic..
I do think the best option is going to be buying an inexpensive compact reliable car and driving to the Bay Area with whatever we can fit (without a trailer) and purchasing what's needed when we get to California.  The main thing I'll miss is our nice bed, which I wont be able to sell for much in Chicago and will need to buy new in California (Wife definitely won't go for a used bed) which, depending on what we go for can be pretty expensive.  Here in Australia we knew we would only be here for 2 years so we bought a bed setup from IKEA that has worked out well so far.  For longer-term use I'd probably want a regular mattress though.

It looks like you've made up your mind on this already for the most part, but I may have your solution...try looking for a 2011-ish VW Golf TDi. The one below is from a dealer, so I wouldn't necessarily buy that one but it gives you an idea of what you can expect.

https://chicago.craigslist.org/sox/cto/5415667248.html

Why? It has a ~3300 pound towing capacity and gets very good highway mileage. Because VW is still mired in trying to fix/make amends for its diesel scandal, prices have dropped due to unfavorable public opinion. Diesel engines are notoriously reliable and will probably outlast much of the car. Even in CA, there are no issues with purchasing and registering an older "cheating" diesel, and with a fix coming in the near future, you won't have to worry about the extra pollution for long.

If you drive it less than ~6k miles a year, you could anticipate getting at least 10 years out of it, with only one required trip to the dealer to refill the DSG fluid (or, you could even learn to on your own!)

Of course, other options on here are just as good for your needs. I would highly recommend a ~2012 Mazda3 with the 2.5L SkyActiv, A Toyota Matrix (side note - if you can find a low mileage, low rust Pontiac Vibe then get that - it's a Matrix in disguise), or an older Subaru would also be good options if you are looking to tow.

[CanuckExpat]

Edit:  Worth mentioning, I know the Honda Fit will come up as a suggestion.  While I do like the Honda Fit for it's "magic seats", I find they're a bit loud while driving on the highway.  On top of that compaint, they generally sell for more than most of the other cars I've listed (including the Civic) which is odd to me.

I was going to throw in the Honda Fit as a suggestion, with the caveat that they can be hard to find used at a reasonable price. We really like ours and the "magic seats" do make it pretty practical. I haven't noticed the noise thing, but I suppose our driving could be minimal. Could it be a build quality issue with a specific car, or different on various model years?

Then again, my first car was a mid 80s Honda CRX which was like driving with only 2 cm of cardboard between you and the rest of the world (I love that car), so the noise thing might be relative.

[RobFIRE]

So Chicago to SF is about 2100 miles. Presumably will take you 3 if not 4 days. The car's fuel economy must be 50 to 100% worse with a trailer, so I don't know US fuel prices but in the UK that would be GBP 400 or more. So say $500 in fuel as fuel is cheaper in the US. Plus 3 or 4 nights of hotel/motel plus meals. You say trailer is $500. So it's at least say $1200. Personally a four day road trip doesn't sound that appealing to me. If you say you don't have much stuff you really want to keep, I would look at selling all furniture, taking economy flights carrying 1 or 2 suitcases each with essentials and valuables, then ground shipping yourself your remaining stuff. I don't know ground shipping costs in the US but surely you can ship 3 or 4 large boxes to arrive a week later for $200 or so? Repurchase similar furniture in SF.

Car when you get there: if the majority of use will be commuting and general local trips, a used Nissan Leaf electric car. Significant costs savings in use due electricity versus fuel cost, and US pricing on used leafs seems pretty good given there have been three generations of the model so the older ones have been sold new at big discounts, making the used ones even cheaper (something like new ones in Colorado were at one point $10500 as $10000 off full price plus federal and state electric vehicle tax rebates of another $9k or so).