Re: Making a living as a liveaboard
Working while voyaging has been a dream of mine since I began sailing in the early 60's. Unfortunately, it really is not something that can be easily done.
As mentioned above, most countries will not allow non-citizens to take work from locals, so you must find something locals cannot do, like friends who got the contract to set up the government computer network in Samoa, when there were very few computer literate folks out there. As a captain or crew or fisherman, etc.; forget it.
Deliveries are a good source of income if you choose to be in an area (like the VI) at the end of the charter season, but you must leave your boat while on delivery; not the best plan, especially in hurricane season. And 95% of sail boat deliveries are plagued by break downs, unreliable equipment and worn out boats, or the owner would do it, because a delivery is just like cruising, but for money, right?
A few folks I know make some money sewing, doing electrical, mechanical and refrigeration repairs on cruising boats. But cruisers are notoriously cheap and if one is a capable professional, most cruisers won't pay for the quality work, which leaves you making little money doing a less than proper job. Also this is not a steady income.
Then there's chartering. The pie in the sky; sail and earn thousands of dollars a week. Well, the booking agents have a saying; you are only as good as your last charter. Which means that if you have 25 perfectly fantastic charters and your last one was with a really unpleasant creep, you will not get another charter until the agents are desperate and need you again. Giving someone a great vacation aboard your cruising boat is not an easy thing to do. You must be pretty familiar with the area you are sailing in, be able to provide 3 full, extraordinary meals and afternoon appetizers each day, never mind the little things that aren't in the "guide to successful chartering". With the internet, it is possible to get a few bookings a year, but again, one unhappy customer can ruin that, too. Getting hits on a charter site is not all that easy, as we can attest.
I would suggest amassing a bit of cash and investing it in an annuity which will give you a steady, reliable income, because, unless you get extremely lucky, you will not be able to earn enough to live comfortably on while sailing.