I fly corporately for an avionics manufacturer on the side and get the priviledge of flying a variety of GA planes to tradeshows/demos and my favs are as follows:
-Mooney Ovation 2, it's fast and has looooong legs
-Cirrus SR22 G3, same as above, just dont get slow on short final
-RV8, flies like a baby-doll and great fuel burn. .
-G36 Bonanza, Cadillac and anyone can land it well (even my zero time wife), terrible fuel burn though
-North American Navion, army tank that is light on the controls and very comfortable
of course i could afford to own none of the above at a half mil per (except the Navion). . .so here is my list of affordable fun planes:
-Luscombe Model 8, metal frame, excellent fuel burn, agile, easy/cheap to maintain, relatively fast
-Super Decathlon, one shouldnt be able to so easily scare another human for this cheap (be careful of the wood spar inspections)
-T28 Trojan, the most affordable way to have a real radial warbird, tricycle gear, less than 200k if you shop around
-Yak 52, simple, aerobatic, plentiful, cheap, pretty fast, metal
Finally, as an A&P IA with about 15 years of messing with the above mentioned (both breaking and fixing), i will list the absolute must do's if you buy an airplane:
-have an IA do a pre buy inspection (research all AD's and make sure log books are complete)
-get one with a fresh annual so you have time to get acquainted with it before it drops dead
-research maintenance requirements (some airplanes cost as much as 2-3k total to annual)
-unless you need it, just get a VFR certified plane (keeps it much simpler)
-make sure the engines are low time SMOH unless you want to turn around and drop 25k
-research accident history, some things are acceptable some are not.
-if it's dope/fabric. . .buy carefully as it is expensive and time consuming to refurbish (the right way)