as everyone has stated, you don't make enough money to afford your own big boat, you spend your whole summer working on other peoples boats, you end up not wanting to be on your own boat after a while. And people suck so really any job in customer service is brutal!

I would look into another line of work for a second career.

Id do the schooling and become an Accredited SAMS surveyor, you are the boss, set your own schedule and prices and from what I hear there's room for more, personally I wouldn't get into the mechanicals I'm done crawling around in bilges....:D

There's a need for stripper pole installers and repairs.

Totally agree! There are LOTS of marine careers out there that do not require turning wrenches, or having to hire competent people to turn them for you.
Most do not realize how much cash it takes to start and cash flow a business until it is sustainable. Imagine what it costs just to keep a few mechanics on the payroll through a long, cold winter (assuming that you are in the north).