" If it really costs $50K a year to maintain a cruising boat.... "
If you have to say "if"...that means you aren't sure of what it will cost. You need to find that out FOR SURE before starting. Don't forget, you will need COMMERCIAL insurance
, you will pay COMMERCIAL
dockage...are you sure you have everything itemized, including the costs of that captain
, hauling, bottom painting, being out of service
while things like that are being done?
And as Ted says, speak to a tax accountant, preferably a CPA or EA (IRS Enrolled Agent) with some knowledge of vehicle leasing companies. The IRS's preferred way to make sure things are proper, is for you to set up an independently run company, with a broker and captain booking the vessel to the general public, and then for you to charter it on the same terms as everyone else.
If the company makes a profit, you get "your" money back. If it loses, you lose. If you lose for something like 3-in-5 years, the IRS is less likely to disallow everything as a hobby, if it was properly set up as a business in the first place. Whatever your options are, once you commingle business and pleasure, the IRS starts getting interested. Speak to the accountant first, and make sure to follow what the IRS accepts as proper, or they may take your shirt. Not to mention, the boat.
And if you speak to any charter company--they'll all tell you you can make big money in chartering a boat. Yeah, sure, that's why they are asking everyone ELSE to put up the money, instead of using their own. Uh-uh.