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Well, Im partial to A4s especially the B5s (1996-2001). so I think they're the best looking. Also, you can easily get into them in the 20s. Go for 1999.5+ those are the "best" years. the 2001s I think have the coil pack problems, but they're being fixed free by Audi. 20s (USD) should get you a nice low mileage Audi Assured A4 with a nice warranty.
As for engine choice, either 2.8 or 1.8T. the 1.8Ts are more conducive to mods, especially chips. But if you want a smooth, lower maintnenance (not low) engine, get the V6. I say lower, not because its less expensive, but the intervals are farther apart.
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