Q,
The 195 is an absolute stunner. Never flown one but they do look the business and the interior is so classy (as is the Staggerwing) They are among the most beautiful aircraft in my opinion.
The 185/180 are probably more practical than beautiful but can certainly do the job, so I understand.
I have no experience in flying any of them but am sure that a man of your standing would be fine.
I do since a few weeks have got some experience in our 'new' Maule an M5 235 which we bought.
It will do all the things you are looking for and to swap over from the Cub is not going to cost you the earth either.
The shortfield performance is great and it will carry 1200lbs @ 120KTS.
Come and have a play if you are around this way.
FD