I'm just starting my hopeful airline career, so i don't have the perspective you are looking for completely. That said, I've owned 4 airplanes and grew up in a flying family. All my closest relations are ex-military now airline pilots flying little airplanes on the side. Seems like most guys i fly with want one of three things; super simple and slow (cubs). Something rugged (skywagons) to take them to the back country, or slick 2 seaters with capable panels to go places "immediately" so they don't have to mess around with non-rev and they can still get "upside down"....like an RV-8.

I take a yearly trip in mine to the back country with a group of friends that all have the same type of plane. Short (1200') strips in the mountains next to good fishing and camping and no cell signal.