Great idea. Thanks a lot. (We've corresponded in the past.)
We are currently in the Riverview FL area part time in the winter, and will become full time snowbirds in the future. Oct-May is great.
We do like the Ft. Myers area, and toured the new Babcock Ranch / solar city development last month. There are several slalom courses in the Ft. Myers area, and I believe there is a healthy waterski community.
I currently drive 25 minutes to McCormicks and 35 minutes to Mulberry. I've driven to Orlando for some lessons with Matt Rini too. No issues. All good.
The newest boat or the latest and greatest Zero-off is not important. A reliable boat is important.
Many clubs or slalom lakes have a comfortable covered resting / socializing area near the dock. Eden ski lake's is one of the most beautiful (screened, hot tub, couches, etc.). McGuiness, McCormick, McClintock, Matt Rini, Swiss are all very nice too.
I'm not sure you'll need to worry about too many members. Getting enough active members may be the target.
Shared driving is fine.
Westend Slalom in Atlanta has a significant flat fee, and then pay for fuel.
Haidweiher in Bavaria/Germany has a small flat fee, and then charges by minute of boat running time. They have Tennis on site, and have a Tennis membership only too, to help cover costs. www.haidweiher.de
My wife sometimes complains when she tags along with me. She would love to see a pool, gym, etc., so that the non-skiers can enjoy themselves more. Wishful thinking, I know.
Good luck, and looking forward to meet.