I'm not a full-time liveaboard, but I have been on-board for the last couple of months and you can definitely make it work.
Sailing is labor intensive, but not in the ways you imagine. Navigation, docking and provisioning are all straightforward.
Where it can sometimes feel like a full-time job is maintenance. Everything on a boat wants to break all the time. Doesn't matter if the vessel is brand new or 40 years old; finding a balance between maintenance and life is difficult.
Pipes are made from plastic and last decades, but they're generally not too hard to replace though.
I'd argue the biggest maintenance jobs to a house is keeping everything clean, basically the same as a boat. The other one would be painting every couple of years, and of course garden maintenance.
That said, unless you are able to drop anchors, I am guessing that you would spend most of your working hours at a dock or with a partner piloting instead.
It will not work either far away from the shore.
On certain routes, packets will be artificially delayed so that high-speed traders can pay big bucks to get their packets through first, ahead of fiber. And, maybe pay even bigger bucks to prevent their competitors from getting their packets through as fast. Imagine tiered pricing, where each millisecond ahead of the rest of the pack is ten times the price.
So, for example, orbits inclined near 70 degrees pass near New York and London/Frankfurt. Packets going by satellite laser links can get there many milliseconds ahead of those poking along on subsea fiber. Somebody in London who finds out 10 ms before everyone else about a price change in New York gets to make a killing trading on the exclusive information.
Regardless I just don't see SpaceX as the company that doesn't evolve with times tbh.
"Evolve with times" does not seem to mean anything. In markets where Starlink is viable, they have no effective competition, and can charge as much as the market will bear. As long as they have more potential users than bandwidth to sell them, they are under no pressure to reduce prices or give up profit. A goal to subsidize Martian colonization provides a very strong incentive to maximize income. We should expect to see very high gross margins until other constellations begin to compete.
London/New York doesn't seem like the distance that there is going to be huge wins for back bone connected entities. But I guess that even if you can land a percentage of packets quicker via starlink, then there is some value in the trading world?
Compare to fiber. Best ping time is 76 ms, or 38 ms one way. So, our budget margin is 10 ms. Suppose, instead of a direct downlink, packets are dumped to a nearby hub and carried via 1000 km of fiber to the destination, with various routing delays, adding 5 ms, leaving a 5 ms lead, 5000 microseconds.
In finance, we say a microsecond is an eon, a millisecond an eternity. That is because in a microsecond we can do >1k multiplications. 5 ms is time for >5M multiplications, many more than needed to evaluate a position and choose a response.
The only routing choices are which satellite to uplink to, and whether to forward or downlink each packet. Whatever choices are made don't need to be re-evaluated more than per second. Packet queuing delay can be negligible; modern switching equipment will start forwarding a packet while the rest is still arriving; this would happen when forwarding via laser link.
The latency advantage for New York/London/Frankfurt <-> Singapore/Tokyo/Hong Kong would be even more compelling.
There are many things rich people can do, poor cannot. You gotta have money, to make (real) money. Thats the harsh truth and most of us who do not have it, have to struggle hard, to make some wealth and very, very hard and be very lucky and gifted, to get rich by it (without negating all ethics).
Someone should always be on watch if possible. It doesnt always happen as people do solo voyages. Open ocean most vessels would have transponders but if you're anywhere coastal you couldn't take the chance as smaller vessels don't always have and you can't rely on radar either.
I do think you could make it work though. Similar to van living. Plan your legs based on availability. You down time will be part maintainance etc.
I wonder now with post-covid remote working options and starlink if you could actually make it work.
I do wonder though if sailing the ship is basically a full-time job in itself (navigation channels? Docking at foreign countries? Getting food etc?).