Re: Question regarding sailing opportunity.
Let me offer you the example of my introduction to sailing. Perhaps you can find a similar entry in your locale.
About five years ago I began volunteering with an adaptive sailing program on Lake Michigan in Chicago. I volunteered as able bodied crew on small sailboats where people with disabilities were learning to sail. In that process, I learned the basics of sailing. I knew very little about sailing prior to my volunteering.
As a result of my volunteer work, I met several skippers who were also members of the local yacht club. I received invitations to sail with them on their personal larger boats. I also received an introduction to the local yacht club where locals without boats can join for about half the cost of regular boat-owner's membership. At the yacht club, I furthered my education with a class or two on sailing.
I also showed up on the docks on the local race nights and asked around if there were boats needing crew. These guys are always looking for ballast (fondly called rail meat) and people to man the winches or whatever. You need next to no experience ..... just a can-do attitude.... and a six pack of beer to get you on a boat.
After a year or two of that I was hooked and gained more and more experience. Then one day in the bar somebody told me of a boat looking for crew from Bermuda to Maine. A buddy of ours had to exit the trip because of weather delays and his need to get back to work. I flew out to Bermuda the next day and did my first Atlantic crossing.
..... and the story goes on from there. Find some way to get yourself introduced to your local sailing community.
If you want to get into this commercially, then check out MPTUSA.Com and arrange to take the STCW Basic Safety Class. That experience in and of itself will get you lots of introductions. But you really ought to have some boating experience prior to that class.