Re: Seeking a solo skipper doing the live-aboard thing in the Caribbean.
You may try sailopo.com. Hank may be able to find someone to take you on.
I would recommend some short trips first.
You will have to come up with more personal information to even get someone to want to talk to you.
Hopefully you have some skills or experience to offer.
Doesn't have to be a solo sailor either. Sometimes couples with children like to have a spare hand as caring for the boat and children can be difficult.
The lesson from the Icarus story is not about human failing.
It is a lesson about the limitations of wax as an adhesive.
If you have an engineering problem solve it.