Weekend city car, practical needs, but want something I can track occaisionally

So, you say your ideal is a wagon, but you list preferred body styles are coupe or sedan. My inclination is to recommend a 5 door.

With you wish list for A/C seats, I'm thinking a higher end make might be of interest, Audi A3 comes to mind, but repairs can be a bit expensive (relability reports here have this model "average").

I rented a Golf 5 Door on vacation recently and liked it quite a bit. I'm not sure what they have for high end amenities. Another well reviewed vehicle is the new Ford Focus ST, but probably not something you're going to find for <$20K given they are 2013 model year or newer. Cars.com shows a couple at $21K so if you're really good at bargaining maybe.

The other one that I think fits in this group would be a Mazada3 (possibly the Mazadaspeed3)

I'd also recommend the Focus ST, or the Fiesta ST, though it may be too small.

I agree with the above suggestions and would add the Subaru Impreza or Outback Sport. These cars are bullet proof so you should be able to buy used and not worry about reliability. Subaru owners are usually not hard on their cars so a used unit would be less likely to have been abused.

It sounds like you really want a BMW. You can get a 2008 328i wagon within your budget. Power is really only necessary when there aren't a lot of curves. Just work that shifter to get the most out of the straight six.

These are looking bad in our stats right now, but I think the end of the CPO warranty has something to do with this. The 2007s are now looking better than they did a year ago (if still not very good). In general, buying a six-plus-year-old German car is a crapshoot. You could end up with no repairs. Or with some very expensive ones. But most likely with a few that are manageable.

If you're willing to get a front-wheel-drive hatchback, then check out those suggested above to see which you like best. Or, for AWD, a WRX.

A NEW Kia Forte5 SX isn't quite as fun as the others, but does include a cooled driver seat with an MSRP of $23,900. If you can afford a $20,000 six-year-old car, you can afford a $23,000 new one.

One off-the-wall suggestion: the most fun I've had on the roads of West Virginia (just drove from DC to Detroit) is in a Mazda RX-8. Outstanding handling, cheap to buy, and child seats will fit in back (much larger and much easier to access rear seat than a Scion FR-S or Hyundai Genesis Coupe). No torque, but on mountain roads this isn't an issue. Just keep the revs up. Fuel economy is only high teens to low 20s, but this probably isn't much of a consideration since you won't be driving it much.