If you don't mind me asking, how old are you? Do you still have a job or freelance? Or are you living entirely on savings at this point? Did you buy the boat in Europe or sail across the Atlantic?
Bought boat in UK, sailed across the English channel a few times and then down Biscay, Galicia & the Rias, Portugal, up the Rio Guadiana (amazing), through Gibraltar, Costa del Sol (yuck), Baleares, Sardinia, Sicily, Greece, then Sicily and Greece again (because Greece is great and also because Covid). Couple other trips on friendboats.
Atlantic crossing E-W with the trades is no big deal, but going the other way (Americas to Europe) can be scary and is not for inexperienced sailors.
If the Med is your dream, might be best to buy a boat here instead. Boats that are great at ocean crossings aren't best at Med sailing and vice versa.
Electrical: 110v 60 Hz, 220v 50 Hz and 12v for 12v DC for electronics while you run 24v dc for the rest. Networking radars, GPS, AIS, plotters has become incredibly complex.
Sewing: having a commercial sewing machine has proven to be useful (to make friends). Repair sails, awning, various canvas
Digital media: most popular boats have satellite com on board and produce one quality youtube video every week. Photos, blogs, manage fans on Instagram. You were hoping to get away from the hustle? You will be back in it quickly.
Refrigeration skills: get yourself a set of gauges ($50), vacuum pump, several cans of refrigerant, soldering equipment. Whomever can produce cold (freezer, cold beers or ice cubes) is king in the tropics.
I can add to this list. The world of handymen is incredibly unskilled. Come with a mechanical engineering or EE/CS background, you will be making friends faster than you can think.
There is a subtle assumption here in your aside remark that you think those interested in sailing are also interested in being popular doing it, probably because you’re interested in being popular doing it, and are very, very comfortably the outlier in the global sailing community. I’ve heard this from some hands, too, who are obsessed with the appearance of the vessel when near harbor.
When I bought my boat I didn’t see Instagram fan management nor sailing for others in the requirements of taking care of it. That’s your interest, and casting it as an inevitable future of boat ownership is almost as insufferable as what’s happened to camping and vans. Please keep in mind that most do pursue this hobby precisely to avoid getting on with that faff, and your experiences make you unique, not representative of ownership.
The experience is for you. Share it with those you love. That’s my take, and we will clearly disagree, so don’t think I’m trying to convince you. I say that because you’ve just become an advocate for sailing in this thread, and I’d rather the vast majority of people who find that type of thing intolerable don’t come to think it’s all sailors do and get turned off the hobby.
A couple things. OP is specifically referring to how people make money while sailing (non-commercially) indefinitely, not hobbyists who presumably have a day job, a traditional source of income, or are retired with savings, and sailing occasionally. Also, OP caveats their assertion about social media posting schedules with "most popular boats" - not simply most boats - it's in your quote. If you're not pimping your boat and yourself on the gram (or wherever), you're boat's not going to qualify as popular, and the statement will not apply to you.
It is positively horrifying that some people set out on a hobby to fulfill others, and also that we’re establishing that as financially rewarding. Sailing, in particular, is about returning to the sea and charting your own path. There’s varying levels of mysticism to that in peoples’ relationships with it, but most entry-level zealots, even, would cock their head at the notion of spending your time sailing caring what other people think about it. What is the point of a hobby in the end? If you want a business, call it a business. A satellite dish for YouTube posting means your sailing is a business. And that’s fine. Just say that.
I also considered your entire litigation on the precision of the person’s language before even creating this account. It’s telling that your substantive rebuttal is lawyering the language, not addressing the point. I considered your “couple things” before you said them and disregarded them. You’re arguing that 10% charity in comprehension dispenses 100% of the point. Unsuccessfully.
People have ideas about remote work on board, but for various reasons this rarely works out in practice. Internet connectivity is poor and intermittent, your schedule is ruled by the weather and having to work seriously distracts from the fulltime job that cruising is by itself.
There may be a mobile base unit at some point in the future, but it will be comparable to the current Fleetbroadband units and therefore too power hungry and too big for your average cruising sailboat. Essentially you need a motorized dish which tracks and counteracts boat movements the entire time it's active. That's what is inside those Inmarsat domes you can sometimes see on big racing boats with satellite uplinks like the Volvo Ocean Race.
Not at all true with Starlink, it uses a phased array antenna to aim the beam at the satellite; everything happens in software. What _is_ needed is an accelerometer which can "know" the boat's movement and then adjust its aim based on that. Seems like they're not quite there yet, but there's no reason this can't work.
I did a few RYA training things that cost a lot of money and got me some papers that nobody ever wanted to see (they're important if you want to charter a boat though). You can just buy the syllabus and gain the knowledge by online learning or video courses instead. I recommend going that route - the knowledge in the syllabus is important and very useful. The formal course in a classroom and the certificate are not. Practical knowledge is gained only by going sailing, making mistakes and learning from them, but it helps if you know the knots and the parts of the rigging beforehand.
But the real learning only begins when you get your own boat and have to fit it out and keep it going. Boat maintenance is hard and there's a lot to learn. You can initially substitute money, but that stops working once you get to remote areas where there is simply nobody else to pay to fix your boat and you will have to do it yourself or give up. Many decrepit boats in remote locations are on the market very cheaply for exactly that reason.
Brings to mind this interesting story of a race like that gone wrong: https://youtu.be/h0WgqMn5lTI
We've got a fleet of 6 27' - 30' boats which are great for day sailing and week long vacations.
1. Watching a lot of YouTube, see my list of channels in another comment, and the note about not believing everythin they do is correct.
2. Joining the local dinghy sailing club. It's cheap, and although I don't really care about racing the skills were mostly directly transferrable to larger boats. Plust contacts are really useful.
3. Get on other people's boats as crew. I own a 43ft yacht, my friend sails it with me. It costs him nothing :)
Later, when you have tried it out and got some experience, take your Day Skipper (RYA) or equivalent course (the ASA in the US runs some). You should at this point have a reasonably good idea of your skills.
At some point in the process, start looking at yacht listings. Yacht World would be a good start. Get an idea of the market. You will work out how much you need to save, and what sort of prices are reaonable.
If you aim to do this on a budget like us, you best be good at fixing things. Plumbing, rigging, engines, fibreglass repairs, more plumbing, sewing, electrical and electronics problems, etc.
The reward is remote anchorages where you're away from everyone else and getting absolutely unenthusiastic about yet another spectacular sunset.
Also dramatic moments in storms, dragging anchors, other boaters being incompetent and inconsiderate, many great friendships and a spirit of community amongst other liveaboards like none other.