I think I've mentioned this in a previous post (perhaps in my Evo thread?), but I was originally considering the Golf GTI. If your budget is US$25k or less, the GTI may very well be the perfect car for you. It looks reasonably sophisticated (more so than the outgoing Golf), has a peppy lagless turbo engine, gets pretty good gas mileage (probably up to 32 mpg or so in North American versions), decent storage space (thanks to its hatchback layout), and can be parallel parked pretty easily (since it's a short car). Maintenance and wear-and-tear items on it should be reasonably cheap, especially if you stick with the stock 17" wheels and tires.
If you get the DSG-equipped version, you'll have a good time with it. The shifts are perfect, but what I didn't like was the fact that automatic shifting is always the default program (unless you're going full throttle). I'm not sure if there is a way to turn it off, but when I test drove one, I couldn't find any switches and the salesman said he didn't know of any way to select which mode (manual or auto) is used. Even when I wanted to manually shift myself with the paddles, at regular rates of acceleration the car would shift on its own sometimes even though I wanted to stay in gear for a little bit longer. But the shifting mechanism is instantaneous and flawless... minus me not finding a way to stay completely manual.