I think you need to look at a few ways.
Tax advice from the Internet
is not worth what you pay for it. Your state laws both for your side of it, the business side of it, and the taxes
at time of sale
are not the same all over. Unless you can depreciate the boat you'll pay capital gains taxes
as a company and sales taxes as a buyer. All this is up in the air depending on where you live and or keep the boat.
Now just look at the charter side of it. Chartering a 30 ft boat will be difficult - it's too small. Charter boats for top tier charter companies are ordered by them per their specifications and you hold the bank note. You need to get down the food
chain before you can offer a boat you already own into charter. People that charter want nice new boats with room.
. It costs more if you charter the boat vs if you don't - quite a bit more. Not a problem with the top tier charter companies since they pay for it.
Unless you really want a much larger nice boat you are just going to go through all the hoops as if you did and the ability to save any money
seems more doubtful. Take the same pot of money and let it generate interest and charter a boat for your own use until you are ready to own and use a boat. This is the sweet spot for doing charters. Not being able to use a boat is the first indicator that you should be selling not buying. You should be doing the charter yourself - not someone else. You probably would be better and money ahead in a 33 to 36 ft used boat
you buy when you are ready to own.