Yeah, I had no idea how involved it was until I went on a week long YT solo sailing across the <insert body of water> binge. Mad props to those people.

Working on vacation isn't as glorious as you'd imagine either.

Your family is on vacation meanwhile you maintain boat, plan, organise visas & paperwork, cook and also make moneys...

And rig their gear.

True, it is involved, but any more than living in a city? Maybe sail a few days then stop in port for a week or more.