Copy/pasted this from my post on Reddit. I hope the formatting stays!

First off, I am a gearhead who enjoys all things cars and motorcycles. For the last five years, I have daily driven a bolt on LT1 Firebird with a 6 speed. I still love driving that car, but it is to the point where one small thing after another is breaking on it (as will happen on 20 year old cars). I have plans to start a three year grad school program next June, so I am looking to sell the Firebird and get a newer, reliable, and more practical car for commuting that I won't have to worry about fixing every other month. A car easy to work on for a driveway mechanic would also be nice, although anything will feel easy after working on the Firebird for the last five years.

My grandma's recent passing left me with some money to put toward a car, and since I know nothing about buying a car built in this decade, I'm coming here for help!

My preferences:

  • New or used under $20k
  • Reliable
  • Standard Transmission
  • Wagon (next best would be a hatchback)
  • Has the ability to tow a small trailer with a motorcycle.
  • Under 50k miles

The car will see snow, but I made it through a couple winters in the Firebird so I'd be fine with RWD.

Cars that have caught my eye:

Fourth/fifth gen (03+) Subaru Legacy Wagon:

Pros: Wagon, AWD, can find some with a manual transmission, I believe it could do light towing fairly easily.

Cons: Difficult to find with low mileage, difficult to find a manual transmission wagon, head gasket issues (?)

Subaru Outback/Impreza/Forester: Seem like they could fit the bill, but I need someone to explain the differences between these cars to me.

Mazda 3 hatch:

Pros: Fun to drive, reliable, MPG.

Cons: Not as much cargo space as a wagon, I'm not sure if it could tow a motorcycle

Please, Oppo, grace me with your car buying knowledge! I'm sure there are a few good car options that I'm not even considering right now. This is a huge sum of money to me, so I want a car that I will be satisfied with for the next 100k miles!