So, as someone who actually lived for a bit on a small sailboat and may well go back to that life, I have a few things to say.
First, think of the worst case scenario. If you're living on solid ground, be it in an apartment or a house or whatever, the thing you do in an emergency is call 911 and then groan about how slow they are. Perhaps you make an effort to keep yourself or your things or whatever is in danger safe until they get there, but you know eventually they'll get there. If they didn't get there in time, you deal with the insurance company to get some degree of money back for your stuff, your house, your health. You may end up in debt, you may end up worse off than you started, but you get a chance to bounce back.
If you live on a boat, and ever leave the coastline behind... The worst case scenario is anything happens that you can't fix yourself. Anything. Imagine climbing a wet metal pole that's at a 45 degree angle due to the heavy winds tearing at the sail you can no longer drop because a line snagged on the roller. You fall, you're lucky if you die quickly. You fail, you're gonna roll and you're lucky if you die quickly. You make a mistake, you fall, see step one. You can call for help, but help has to find you. Help has to be in reach. Help has to be able to navigate in the wild weather, where they might not even spot you at close distance due to the height of the waves... Even if they KNOW where you are, you won't survive until they get there unless you take your survival into your own hands and get that line unsnagged.
But that's the worst case "holy shit I fucked up and took a gamble on a weather report" sort of scenario. It's very unlikely to happen as long as you are very careful to stay within your limits. Think of the bad scenario. Think of slipping on a wet deck and breaking a leg. Oh sorry, you might still wish you had died quickly. Help is still far away, it might get to you in time, but if it does you have to abandon your home, which may not be there when you get back.
That being said, living on a boat is lovely. The worst case scenario might be harsher than it is on land, but you can limit your risk by being careful. You just have to be aware of the worst case scenarios so that you don't take risks without thinking about it. You can't go on living with the mindset you did on land, or you'll be an accident waiting to happen, and accidents on the sea are BAD.
So, this is where I mention that I didn't take my own advice. I had never sailed a boat before I sat down to take a "test drive" with the guy who sold me what turned out to be my home for part of a year. Never even been on a sailboat before then. A week later I was setting out, thankfully in as good weather as the forecast had told me, learning as I went what I hadn't already picked up from sailing forums, books, videos, and even sailing simulator games. Basic sailing isn't hard. I stayed in fairly familiar areas, navigating with software on my phone, charging my laptop and phone with an overpowered solar power system. By never being more than a few miles off the coast of my home country I pretty much had constant mobile internet. I have never slept so well, as on the two inch thick old compressed foam mattress in that boat.
I have never been so free.
It was worth climbing that mast in a storm for me, at the time. Would it be for you? For all future?
Find a sailing school, get some experience. Rent a sailboat or part of one over a summer. Experience the lack of privacy when you have guests on board. Experience the freedom. Experience the cold fear when the weather turns. Then think about it again. It'll be cheaper that way.