noob question

Hi. I'm not sure if this is the right forum to pose this question, but would greatly appreciate any feedback.

So I recently retired from the military and have big dreams of cruising as a lifestyle. I sailed lasers on a lake as a kid, but that's as far as my sailing experience goes. I've read some and realize the best way to get up to speed is to take lessons and join a crew, to not only see if it's really what I want but also to gain experience.

While I plan to do those things, if I were to try to get a job in the sailing world, where should I start to best prepare to live my dream?

Being a military retiree, I'm not wealthy, but I also don't need a full-time/career type job, unless it is more beneficial to pursuing my dream than, say, a part-time job at a sailing gear shop.

Due to family obligations, I can't join a crew in the near future, but I do live in Los Angeles.

Any advice? Thank you.