Re: Renting?
Would you rent your boat through a company that would give you complete insurance coverage, and an on board licensed captain?
I think you asked a good question to the wrong crowd. A program that you (briefly) describe is for chartering large yachts. Almost everyone who participates in this forum owns a small recreational motorboats--not the kind that would be part of such a program. You can expect a series of almost angry "no way" answers, as if you proposed renting their daughter. Many of these are people who would never even lend a boat to a friend or even a family member, a strange concept to me.
Chartering boats, either captained or bare boat, is a legitimate business and reason many people get large boats in the first place. Seems to be done a lot with sailboats. It's no different than owning and renting out a beach house or even a house/condo/apartment. Liability is covered. You expect some wear and tear. You "furnish" the boat differently just as you do rental houses. People here, however, will act as if they were asked to rent out their homes.
Then there are the boat clubs--I have a friend who is very happy with his arrangement where he sold his sailboat to a rental club, and as part of the deal, gets rental privileges of the boat. He gets to use it as much as he would anyway; he has no maintenance work or expense. Works fine for him. he did not regard his boat as a family heirloom, but simply a piece of recreational equipment.
The question often posed here about private or casual renting a small motor boat correctly raises issues about risk of loss or damage coupled with voided insurance coverage, and the answers will reflect those concerns.
It would make your question interesting if you gave some detail about the boat in question and terms of the arrangement. That would also perhaps deflect responses that would not pertain to the situation.