If you like the 1999-2002 style, go for the 01-02 years. The only reason I suggest this is because the 2000 and previous only had the 3dr with the extended cab (if you are looking for an extended cab). I had a 2000 Z71 Silverado and it was one of two things I didn't like about it. The other was it didn't have leather seating. Other than that, it was an awesome truck. Go for the 5.3 engine if you can afford it. The only way I'd have gone for the 4.8 is if it was already in the plans to drop a 6.0/6.2 engine in there ... but JMHO. I really like my 06 Z71, but it is a bit outside of your price range (unless you find a REALLY good steal on it). I got a really good deal on my truck at $6k under book, but it is still outside of what you want to pay. Anyway, just me talkin' here.