Interesting question Brad; made me think about what I would really like to fly in.
Hands down, it would be an Aero Commander; simple twin, high wing, piston, GA aircraft. And I would prefer the AC520 of all the rest for casual flying.
As a passenger, the best turboprop I ever flew in was the de Havilland Dash-7; quiet, low prop hum, comfortable, powerful, lots of handling finesse, a great experience overall.
I tend to like high wing, STOL aircraft, piston preference. Think de Havilland for most of them. I flew in a DHC-4 Caribou while in Vietnam and was very impressed with that aircraft.