I don't really see the Boxster as a gateway drug
When I started looking for a nice weekend toy 5 years ago I thought I would get a nice 996TT or Ferrari. I drove quite a few but in reality the TT was just too much car (rarely out of 2nd gear in town) and I didn't want to blow $100k over 5 years maintaining the Ferrari. I just wanted a great, fun car to drive for kicks and grins.
I have since driven or been in the right seat of nearly every Porsche model built in the last 30 years. I still love my Boxster but admit to having a sweet tooth for a 987 Cay S. If a really clean one came along for about $25K I may have to have it.