As some have stated the 996tt is a reliable car, I know, I own one and I track it, those who state it is not do not own one. You turbo the NSX and you are asking for more trouble than you may be willing to put up with, like getting it properly tuned and running reliably in all weather. Everyone I have met with a turbo modded NSX or even SC has had tuning issues, unless you are very comfortable with tuning don't do it. The 996tt is factory prepared and at stock is very reliable, when modded you open up a can of worms. Maintenance on the 996 is similar to the NSX, not less but not much more. The clutch is easy to replace as the engine drops right out compared to the NSX, but that is not a routine item. Routine items such as oil are a bit of a pain on the 996tt and the amount of oil is double but so what, you want something special not a Camry, right.
The 2001 996tt is the least expensive and most reliable of all the 911 Turbos and can be had at the upper end of your price range, I know because that is what I paid last year for mine, you have to search but it should be easy as they made a lot of those cars and there is someone taking care of one just for you as we speak. Don't go near any 996s other than Turbo, GT3 or GT2, as they have several engine issues and the Turbo and GTs are a completely different engine than the other 996s.
The NSX is the absolute best bang for the buck and you just can't beat it and it is without question the most reliable of all the cars discussed and probably the most fun overall. But your eyes are wandering so you need to get it out of your system. If you go with the super sexy and exotic Ferraris your bank account will be drained in no time. The homley 911tt won't kill you financially, will put a big smile on your face, but if you sell the NSX you will be back as it is not anything like the NSX.
Good luck,
Tytus