Let me give you one piece of advice somebody should have smashed into my head when I had a small budget and was buying used cars.
The NUMBER ONE priority on your list should be a car that is reliable and that is easy/cheap to repair if it does break. All those things like "fun to drive," "sporty," "cool looking" and stuff goes out the window. Nothing is more frustrating than a car that breaks down and is expensive to fix - doesn't matter how nice it looks or how much fun it is. Even if you get a used Ferrari for $3000, it's going to drive you nuts if it breaks every month.
A car that fits this important requirement really well is the Corolla. They are well built, extremely reliable, and Toyota put a lot of thought when they designed the maintenance items. Changing the oil is easy, changing the accessory belt(s) is simple, etc. A lot of this basic work can be done yourself because it's quite simple. Even changing the brakes is pretty easy (compared to some cars).
As for manual versus automatic, remember that clutches on manuals need to be replaced around 100K-150K miles. A mechanic will charge $600+ for a clutch replacement. A good automatic transmission will last the life of the car (if you change the fluid at regular intervals), and the Corolla transmission is typically well built. Just keep in mind that many automatics are poorly made (Just about every Taurus) and will fail at under 100K miles and cost a bundle $1500+ to replace.
The Civic and Integra are also well built cars that are easier to fix. The Integra is basically a civic in a fancy skin, so you can get Honda branded parts and use them in the Integra. This will save you a bit of money during repairs.
Finally, try to find a good mechanic and take any car in for an inspection before you buy. They'll be able to look over the car and tell you if something is going to break soon, which is really important.
Hope all this helps.