B.B. the addition of a CS prop and retractible gear will of course add to the purchase cost and maintenance cost to some degree, but the increased performance is a reward well worth having.
The difficulty of flying the thing is a non issue, its just another type check out and it is not difficult nor complex.
Where you must take care when flying is using common sense and knowing what not to do.
I'm pleased to see we are back to actually answer people's questions....
I'll second most of what has been said here, there is, however one issue with fixed gear vs retractable. At least
AFAIK, there is no SEP with fixed gear certified for flight into know icing conditions (FIKI). Now, doing that is probably not a great idea in a SEP anyway, but if you want an airplane for business travel, this might be a consideration.