Even from south Cape Coral
, you probably have a minimum 1/2 hour trip to the Gulf. My mother lives on a canal in the SE quadrant, just north of the Midpoint bridge, and it takes quite a bit of time in a powerboat. It seemed like forever in her sailboat!
The Caloosahatchee River looks like a large body of water
, but there are many shallow areas, so it is necessary to follow the channels. Not so important for a sailboat, but there are strictly enforced Manatee zones.
IMHO, I would choose as far south in CC as possible. I have been looking semi-seriously, but it seems the homes in that area are also among the oldest. You are correct that much of Ft. Myers and definitely North Ft. Myers will take longer to get to the Gulf.
As far as working on your boat--the home next door to my mother hired a crew to do a complete renovation
on a 40'+ sports fisherman right at his dock, which took some time. Never saw that he had a problem.
I am sure there must be someone on the forum who can chime in with some suggestions.