OK well you probably aren't going to want to hear this, but it is MMM forum, not some other forum, and you posted here, so........
Key words in your post:
"money is no issue" If you aren't FI, then it is.
"want" Want vs. need.
"monthly payment" Monthly payment is the RESULT of the equation. Maximizing value is more important.
"I don't know how dorky I'll look" Listen... you sound younger and so I understand this thought (hey, I'm 31 and still a little vain). Just because someone drives an Escalade doesn't mean they have two nickels to rub together.
"Don't want to deal with the maintenance thing.." I get it, some people just don't have the mental fortitude to change oil, or their time is more valuable. And even mechanical-minded people don't want to deal with unexpected breakdowns. But by buying your way out of dealing with some issues, you are hurting yourself financially to some extent.
"20 minutes from home" Walk? Ride a bike? OK I am guilty of this one, but I would get roadkilled if I tried to ride a bike to work in my area. Don't know where you live so maybe this is true for you as well.
Point is, get your head right, first. I assume you are on MMM because you are interested at least in how to save money if not FIRE. So I'm not trying to be preachy, just trying to help..
All that being said, and assuming you really are interested in (1) reliability, (2) cost savings, (3) utility, and (4) to some extent, appearances, here is my list:
02-07 Focus ZX5 and Wagon (SVT and non-SVT)
Any year Mazda 3
Any year Honda Fit
Any year Suzuki SX4
Any year Toyota Yaris
Any year Ford Escape (why? I get about 28 MPG in our 2009 Escape with a 5 speed - a little bit better than my Focus ZX5).
Any year Mazda 6 wagon
Any year Toyota Matrix / Pontiac Vibe
Any year Scion xA / xB / xD
Any year Nissan Versa
Any year Mazda 2 (I have seen new ones for $12-13k)
Any year Chevy Cruze / Sonic / Spark (I have seen new / used ones around $12-14k)
Any year Fiat 500 (this is a stretch as they are small, but they are cheap)
The Subarus are ok but unless you need AWD (not just want), it's a waste. Nothing against Hyundais, just no experience with them. Not too many wagons in Honda, Hyundai, Toyota, Nissan form either. There are others, but you get the point.
So all that does is define your population. Gather prices, etc. That will give you price points on what you are looking at. Eliminate any that have a spotty reliability history or that have high parts prices (for the sake of simplicity I would say all of the above would be about the same cost / month reliability and parts prices). Gather MPG figures. Figure your average monthly mileage, and insurance costs for the above. Here is what I do for Total Cost of Ownership per month:
Monthly Fuel Cost for each option - determined by MPG, $ per gallon, miles per month
Effective Monthly Payment for each option - This is not simply the price divided by a set monthly timeline. To be more accurate it is the current value (assumed to be price paid) minus the value at the end of the timeline, divided by the amount of months in the timeline.
Monthly Insurance Cost for each option
Monthly Maintenance Cost for each option
The sum of each of these calculations is your TCO. I'll give you a sample:
My Volvo S40 MFC $142.42 + EMP $13.89 + MIC $60 + MMC $80 = $296
My Focus ZX5 MFC $136.34 + EMP $20.83 + MIC $30 + MMC $40 = $227
A 2012 Focus SE MFC $116.15 + EMP $55.56 + MIC $50 + MMC $20 = $242
So basically this tells me that my most economical option is the ZX5, BUT... for $15/mo I can have the safety and reliability of a newer car, as long as the depreciation is accurately portrayed and there are no other unaccounted for impacts. Of course, your results will vary based on assumptions. Mine:
Volvo S40: 27.75 MPG / Starting value $4500 / Ending value $4000 / Insurance $60 per mo. / Maint. $80 per mo.
Focus ZX5: 28.96 MPG / Starting value $3500 / Ending value $2750 / Insurance $30 per mo. / Maint. $40 per mo.
'12 Focus: 34.00 MPG / Starting value $15000 / Ending value $13000 / Insurance $50 per mo. / Maint. $20 per mo.
All:
Timeline of 36 months
1000 miles / month
Fuel cost of 3.949 / gallon
Questions, ask away.