hooah, I think those 2 drs are friggin nice! I was in exact same boat as you... 00-04 Tahoe, but preferably an 03-04. Or a 97-99 2 dr as long as it had leather and the rear hatch door.
I was searching everywhere and was willing to travel within 850 miles. I went a looked at/drove a few 2 doors. Man, I really liked them, but they were over priced. I had just missed a 99 2 door w/100k & leather for $4500 OBO. I was really bummed, but there was no picture, so who knows. Then, I was trying to negotiate a 99 2 door w/126k & leather. They wanted $6995 at a dealer. Offered them $5500, but they wouldnt budge from $6300. Too much IMO & I had to drive 300 miles RT to get it. I was willing to spend up to $5000 for a 2 dr, $6000 for a 00-02, and $8000 for an 03-04. I was looking in different states, and they are hard to find. Luckily for me, I had time, and cash in hand. If you're not as particular as I was about the options, you'll find one sooner.
Also, another thing I came accross at many car lots: "Gas is cheap now ya know, these big trucks are cheap to drive, and the prices are going up!" Whatever, it could be true, but when gas stays at these prices for 6 mos or more, then, yeah, we'll see. Don't let that get the price increased. I'd say, if you're willing to travel even within a cpl hundred miles, that will give you a much greater market.
That '00 you're looking at isn't too overpriced, but it is a little bit. I've seen cheaper deals, but with more miles. I'd probably pay $6200 for that truck. The 2 door is priced more fairly, but if you get a '97, you get a passenger airbag (which was important to me).