As a Scuba Instructor, I can't tell you how many starry eyed folks come into the shop with "The Dream"....hate the office, life sux, want to become an Instructor, move to the Caribbean and live life barefoot in the sand. The reality of it and the possibility of it actually happening results in disappointment 99% of the time.
This though, has a much higher possibility of success. If I were you, the first thing to do is move. Can't make this happen where you are. Pick a place out on the coast where you can get a good job and slip rentals are cheap. Good luck with that, finding a cheap marina is gonna be tough, but they are there.
Once there and working, find your boat, in your budget, and move in. Spend the next year or two living on the boat, fixing her up, sailing her and getting to know her. At the same time, learn as much as you possibly can from multiple sources about the cruising life, what it takes and how to do it.
Maybe...in a couple years....you'll be leaving your marina behind as you sail away on an adventure you'll never forget!
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1982 Catalina 25 #2897
Eagle Mountain Lake, Texas