[Overdrive]

Write your book, no one's going to criticize, and you'll find your answers, but do try to search the forum first, as you will likely find most of your questions have already been asked in some way.

For the PPI, don't do a dealer, at least not the dealer you'd be getting the car from, obviously. Honestly, better to find an independent who knows these cars.

As I said before, stealing the line from RandallNeighbour, get the youngest car you can afford, and try to go for an S. The RS60s are nice and uncommon, and that mileage is rather low, but also shows that the car was drivena decent amount over 5-6 years.

Wikipedia actually has a good amount of information on the Boxster's development throughout its generations. Give that a read to answer some of your questions about the changes that have occured over the years.

The older your car is, the more money you should set aside per year for maintenance and any unforseen issues. Either way, I'd say have a few thousand dollars at the ready in case anything unexpected comes along, just so it's not such a hit to any of your immediate income. Stuff will wear and need replacement, that's just the nature of machines. These machines tend to be a little pricey when they break, but that's also why it's good to get a certified pre-owned car that will have some items covered under a warranty.

I'd say get the RS60, drive it, don't baby it, but take good care of it...though I'd also say if something younger and comparable comes along for similar money, go for that, and either way, be prepared to spend a little money right off the bat to get the car in good running shape for the long term, as it could be needed.