6 pages of messages?
Maybe we need an article on the pros and cons of having a company (possibly an LLC) own your boat versus personal ownership. And versus having your existing company own the boat (for marketing purposes ... entertaining clients on your boat is no different from taking them to a fancy restaurant ... though likely more expensive).
I'm not a lawyer, but I have a half dozen companies in Canada, USA, and India and pay taxes to both CRA and IRS. I'm an engineer, but I have 6 lawyers for different tasks in North America, plus a corporate lawyer in India.
When I buy my next boat, I expect to create an LLC (maybe a "Close LLC" in Wyoming due to the lower overheads) and have the LLC place it into a charter fleet in Bellingham WA ( a half hour south of my Canadian home). That completely avoids the sales taxes.
I'll charter it in the summer, while I'm travelling inland by motorcycle. I'll live on it in the spring and fall. In the winter I'll be some place warm ... most likely Panama.
(where you pay no taxes on money earned outside the country).
The charter will more than cover all maintenance, insurance, and moorage.
So, now I've eliminated purchase taxes and operating expenses other than fuel.
I give up July and August use. A big price to pay, but I'm happy with that.
Without it being a charter boat in an LLC I wouldn't be able to write off insurance, moorage, maintenance, etc. as business expenses.
I'm hoping that all I'll need financially is a substantial down-payment to have it "float itself".
Please expose the holes in my plan.
I might be missing something that you know of and I don't.