You don't say where. The
regulations are extremely different from place to place.
Issues are likely to be: (a)
insurance; (b) licensing; (c) coding; (d)
taxes.
In most places, a
boat put in charter has to be "coded" -- has to be equipped to a certain standard and inspected and certified. That standard often includes a lot of things an ordinary cruiser doesn't need or want, so expenses are involved.
The worst thing is that the boat is no longer really yours. You have to keep your personal stuff off of it (or locked away), which is really hard. And strange hands will be hoisting (and no doubt, tearing) your
sails and lines, and scratching your
hull.
I think it's a bit like
renting out your home for a few days a month. And I think the answer is the same -- a rental property is one thing, but your home is another. Things not to be mixed up. If you want to charter your boat out, I think you should do it systematically and more or less full time, as a business.
This does not exactly apply to a high end boat with a professional
captain. That's a different situation because it will not be the unknown guests using and breaking your
gear.
In any case, however, the market favors those who charter other people's boats, I think. It's a great deal for the charterer, a lot less than the cost of owning your own boat, and a lot less trouble. I'm not sure it's such a good deal for the owner of the charter boat. Do you really make that much
money, if you consider realistically the wear & tear and depreciation of the boat, which is a much more rapid process when a boat is in charter?