What year Boxster would you get for most reliable?

[Perfectlap]

if you have a 2001 I would get a 2009 or newer.

I was at your same point just as the stock market was crashing along with banks nearly going kaput. I decided against taking on a new monthly payment on the high side.
But here's where I didn't predict things so well. The IMS/Clutch/Flywheel/RMS job costing nearly $3K quickly led to another round of repairs of things that went unexpectedly (AOS, starter, alternartor, coolant tank which of course led to needed suspension work and new tires/wheel dent repair. Just like that... it got expensive quickly. Mind you my car had always been garage kept and driven only on weekends but 10 years takes it toll, things don't last forever.

The thing to keep in mind is your mileage up here in north east. Our cars take a beating from harsher roads and the elements so major maintenance will come around sooner.
If you don't want to deal with all that go 2009 or try and spend as little as possible until you make your move.