[f0rge]

I'm not really sure, a lot can happen in 3-5 years. If I was starting to look now I'd be looking at a used Boss or an NSX, maybe a CTS-V wagon. OR maybe 2 cars instead, FD RX7 garage queen and an e36 M3 track car/winter beater?

Per your Porsche maintenance questions, if you're buying the car you can likely afford to maintain it. You just have to plan ahead, make sure you have $2000-2500 on hand in case something goes wrong and for regular maintenance. My previous car was an E46 M3 and that is definitely on the high side of maintenance but if you plan for the major services and have a contingency for things that will inevitably break then you will enjoy the car and have a great couple of years with it.

It definitely worth paying a bit more up front for a car with great maintenance records and ones that have recent had recent major service done. If someone is anal enough to keep records and do $1500 worth of maintenance on a car they plan on selling then they've likely treated the car well over it's life and you shouldn't have too many problems down the road.

ALWAYS DO A PPI.