Best year for Boxster S?

[kk2002s]

NOT an investment, driving fun and for some DIY hobby.
Your budget gives you a lot of options. Being that this is a 986 forum that is going to be the perspective and familiarity bias you will get here.
Personally with your budget, 2004ish 911 turbo. AWD so you don't have to layup in the winter
I could never comprehend spending $55k-$65k on a new 986 but people did just that and someone did on my boxster
You need to tell us a bit more of your intentions:
Are you a DIY person? Track days? My knee jerk is get 3rd generation 2009+, past the IMSB