Dude, go for it!. I'd start moving now, to MD, buy something 30-ft or larger, move in, sail the Bay, learn, work on her, and then live the dream.
I just wish I bought my boat 20 years ago.
Oh, I, too, wanted to be a ski bum when I got out of the military back in 1977, actually ski patroled a season, then recreationally, until things got so darned expensive and crowded. Got bored with waiting in line for 20 minutes, 5-10 minute ride to the top, then 2.5 minutes to the bottom.
Then, I became a slave and worked, and still work, from paycheck to paycheck, this time with a 23-footer sailboat that I've spent thousands on, after the initial purchase. Getting ready to enjoy the inland sailing season on a very nicely upgraded boat. Just wish I was younger. I'm sure enjoying the hell out of sailing, and it scares the crap out of me too, half the time. Some mighty ugly winds on the Columbia River at times.
But, I'm learning and am fortunate to have befriended two live aboard folks, who both work at the local Chandlery, dock close to my boat, who love to sail, lots!!!!, one on a Catalina 27 tall rig, and the other a 34-foot Columbia (very sweet boat that's been to Hawaii twice).
Best of Luck!!!!! You've found a great place here to get your research done. Listen to these folks. They know their stuff. Oh, you'll want to add the latest edition of Chapman's Piloting and Seamanship to your library. A very knowledgable fellow who used to frequent this place consistently recommended The Complete Sailor, by David Seidman. Get it.