Pete: Never!
Whatever I can fly on someone else's nickel is usually a great bird to fly!! If I am getting paid, so much the better. Mostly anymore, a plane is a tool for me. I use it to access where I want to go. Having one plane is a compromise, hence the middle ground having the Maule. Great bird to hunt with- STOL, fast and will carry a load for much less than the Cessna Counterparts, but handling in the air and ground is not the same. I look at planes a bit differently I guess, a guy really needs two or three actually.
While everyone loves the Beaver, it sucks to unload and load a half ton every 20 minutes- gets tiring. Worse on Wheels!
Some of the most fun flying I have had has been in cubs and my old champ. Light controls and no electric is a kick. Not having to feel responsible to listen and just having ear plugs!!! J-3 is fun also.
Bill Tracy checking me out in the Chipmunk was a hoot! Would not count out that bird or that flight.
The old Stinson Gullwing was like taking an old Buick through the sky... and the Bonanza is quite a stable ride.
So many great planes- but if you wanted to focus more:
Travel: (if not turbine) for me was the Bonanza- fast and stable
Light Controls: Any DeHavilland, Otter was fantastic
Cheap just in the air: Champ/Cub- Cub if windy at all for power
Hunting: -18 hands down
Want to make a statement: Gullwing!
Floats: 180 hp Cub, unless you are working hard then a 185 w/550 and extended wing, sportsman stop; Aerocett Floats!!!!