[Perfectlap]

from a 912 I think you would enjoy the CaymanS the most. Every Porsche guy I know is licking his chops waiting to get in a used one as their 2nd pcar for daily driving.
unlikew me, Roadsters aren't for everyone and the resale values of CaymanS vs. Boxster could not be more different. Too many Boxsters and not enough Caymans. But both very popular.

As for new or used, with a warranty and then an extended warranty I see absolutely no point in buying a brand spankin new Boxster.
You can use the money you save on depreciation for the mods or driving schools.

p.s.
Nearly 24K miles since 2004 and I've only had one repair, throttle body $500.