Ok, I’ll break it down large, I want to see you out here.
1978 Bayfield 29, $11,800 (2018) cash cash, envelope full of bills. I put about another $10,000 into it since in upgrades. Larger anchors, chain, lines for everything, new standing rigging, upgraded electrical, home built LifePo4 batteries, GPS, AIS-B, LED lights, solar, wind, blah blah blah.
My dingy is a 2015 Riviera 12’ fiberglass $1500. My outboard is a 2009 Yamaha 2stroke 15hp $1600.
My rent is approximately ZERO. I pay jack shit to fuck all. I “live on the hook”. I have about $1600 in my mooring (3 anchors, 150’ G4 3/8 chain, crane swivel, floaty thing, two lines to the boat from the swivel).
If I was going to live here forever I would need to plan on replacing the chain, swivel, and the connectors every 3-5 years, just to be safe ($1500 just to be safe). I’m leaving after hurricane season but because I have a mangrove swamp I can hide in up to a Cat3 storm I’m here until Thanksgiving.
I have 550w of solar, a Honda eu2200i generator, a 400w wind generator, and live off of 400 amp hours of 12v batteries (2x200ah). Home built at less than half the cost of prefabs in 2020. I love them so much.
New sails will be about $4-6K. My sails are 8 years old and I’m fully expecting to get at least 5 more years from them. I’ve taken good care of them.
My car is a 2002 Toyota Echo that was $1000, I pay $100 a month to park it about a 1000yards from the public dingy dock, which 99% are free in the US. Down island is a whole other thing, lots of places charge.
I don’t have Starlink. If dickhole ever sells his interest in it, I’ll have it the next day.
You absolutely can do this, but you will need to become radically self-sufficient. I haven’t been to a slip or a dock ( other than fuel) in six years. I haul water by hand, I’m my own electrician, mechanic, sanitation worker, plumber, electric company, you name it. And paradise can fucking suck.
I dont have an oven, don’t have a toaster, I don’t have any heating or air conditioning. I do have some fans. I don’t have hot water unless I put a 20 l can in the Sun. Living this lifestyle is as much about sundowners sunset, bikinis and fun as it is about what you’re willing to fucking endure.
Marina’s will run you from $300 - $3000 a month. They are hot, noisy, you’re crammed RIGHT next to others and they are expensive.
If you want to get an idea of actual prices, take .25 up to .5 off the asking prices for pretty much anything under $80k. Search Tempest for Craigslist, search Florida.
If you decide yeah… I’ll absolutely help your effort and happy to answer any more questions you have.
[edit] Maintenance runs between $2-6k a year. If you preventative maintenance the living shit out of everything, you’ll spend a lot less a year. I do 90%+ of the work myself. I purposely bought a small boat because small boats are small problems with small bills comparatively speaking. And also when traveling to communities that are less fortunate than most Americans financially at least, it’s easier to interact with the locals on a small boat than it is on a large boat because they will accept you much faster than if you show up on a 50-ft plus.