Best way to sell minivan and downsize?

[Biskil]

Good day all,
    I recently discovered MMM via the Tim Ferriss podcast and am in the process of getting my life in order while still remaining on speaking terms with my wife and children (ages 12 and 9).

We recently became a two car family after 6+ years of only having one vehicle. We both work, and commuting by bike is not an option as it was at my last duty station (I am active duty military). Well, I guess it's an option, but it's not an inconvenience I'm willing to put up with.

We have a 2016 Honda Fit and a 2012 Honda Odyssey. Both are paid for. My wife's commute is longer, so she drives the Fit, which leaves me driving an 8 passenger 23 mpg vehicle 30 miles (round trip) five times a week. The inefficiency of this is killing me.

I've pretty much decided on a used Prius (possibly another Fit) to replace the van, but there are several ways to do this, and I am looking for some advice.

Option 1:
See the van on craigslist (should be able to get $14.5k or so), take out a loan to buy a used Prius via Craigslist (spending about $11k), then once the van is sold pay off the loan immediately. We shouldn't have any interest to pay if we pay it off prior to the first payment (I have no idea if this is true).

Option 2:
Sell the van to Carmax, while at the same time buying a used Prius from them. I like the peace of mind buying from Carmax provides (I am NOT handy), but I know that I won't get as much for my van as selling private party, and a used Prius will cost more.

Option 3:
Sell the van on craiglist and get another Honda Fit. I love the Fit, but I'm more interested in a Prius due to even BETTER mpgs, as well as a bit more cargo room for road trips.

Please advise. I'm sure there are even more, better options that I'm not thinking of.

Bottom line:
I gotta get rid of this van. I seemed like a great idea when we bought it as we were living in the Pacific Northwest and taking lots of road trips. We drove coast to coast in it last summer and it was super comfortable. But now I see we could've done it in a small hatchback and spent a lot less money.

[HipGnosis]

Option 2.B
Buy a Prius from Carmax.  Get their buy amount for the van.   
Sell the van on craigslist, using the carmax amount as a bottom value.
If you don't get a better offer, take it to carmax.
I wouldn't worry about paying one month of interest - just make sure you have the funds to pay at least one payment.

But... what 'piece of mind' does buying from carmax give you?  Their warranty is optional, which means you have to pay for it.  You can buy car warranties from all sorts of places, and I'm pretty sure there are better values than the one thru carmax.  I wouldn't pay for a warranty for a Prius, they're very (very) reliable.

[Biskil]

We went to Carmax last night and got the van appraised, and I was shocked that they're willing to give us exactly what I was planning on listing for on Craigslist! Their prices on Prius seem to be kind of high, though. We test drove one at a local dealer that seemed much more reasonable.

The Carmax piece of mind I was referring to was their thorough inspection process. But you're right, the reliability and relative newness of the car we're looking for probably means we have nothing to worry about.

[MightyAl]

On newer cars carmax is a good way to go. I got a car appraisedbthere and they offered me $300 less then I was looking to sell it for private party. Needless to say I took it to avoid the $300 worth of hassle. They are not quite as good on older cars even if the mileage is low. I don't think I would buy a car from them as their prices always seem higher than market.

[Biskil]

I found their prices to be high too. We looked at a Prius there last night, but found one at a dealer that is newer, with less miles, with more options, for less money. Kind of a no brainer. Nice people to deal with, though.

[MsPeacock]

I had a good experience selling my car at Carmax and getting another (cheaper) car there.

They offered me more than KBB for my car.

However, you HAVE TO take any car you buy from them to your mechanic and have them give it a very through looking over. The Carmax "inspection" is worthless. They did fix the problems the mechanic found ( I took it back to the mechanic to confirm the work has been done). The give you something like a 30 day warranty and after that any problems are on your own dime.

I think you can probably do better buying private party in terms of price. For me it worked out because I saved on the sale tax, which was significant because I was trading in a 35K car for a 22K car - and didn't have to pay sales tax on the 22K.

YMMV

[Biskil]

I ended up buying used from the dealer, they had a deal on a used Prius that seemed very competitive, plus they gave us a "deal" on the van trade in that was comparable to Carmax's. Of course a private party sale would've been more lucrative, but the speed and ease of the dealership was too tempting.