Thanks for all the input you guys have provided, in the end the 996 does seem like a wise choice. I will be using it as a daily driver, plus some turbo upgrades down the road maybe in a year or two's time. I'll take a look at the maintance costs first, and see what specialists charge here in my area. But I think oil changes and filter changes I can probably tackle, I'm quite handy and I don't mind getting my hands dirty.
So the best idea is to hire a Porsche specialist and inspect the car before purchase?
Will he do compression test and DME scans? What is the average going rate for these kinda tests?
Also when purchasing a 996TT, where is the best place to pick one up? Is there any specific states in the US which have cars better condition then others? I am located right on top of New York, where niagara falls is. So I think if I'm going to buy a car, I'll either ship it for extra cost or drive it back.