The two big questions, and what determines whether it makes sense or not.
1) how many weeks a year, can/will you use the boat. For it to make financial sense the answer should be at least "quite a few"
2) the value of the boat at the end of charter service unless you are dead set on keeping for private use. Though impossible to know market conditions 4-5 years later, I would use less than 50% of purchase price as a starting point for evaluating the wisdom of it.
Moorings and Sunsail take care of all maintenance and insurance dockage etc. they do limit the amount of time you can use the boat and how much in high season. I believe their monthly payments to you are about equal to the mortgage payment if you put down 20 or 25% and financed the balance over 15-20 years. It varies some with specials on certain vessels. Unless you put more than that down on purchase or pay more than the income on the loan monthly while in charter, you will likely come out upside down on the loan...more balance than boat is worth.
There is a conflict of interests on phaseout of charter. They want you gone and to fix as little as possible. You are stateside. You are at a disadvantage.
Other option is the operations like TMM and others that charge for maintenance dockage insurance etc.but you get 75% of income and can use the boat as much as you like anytime you want. If you have a popular boat that doesn't have a major problem, it is often much better. On the other hand if the boat has say a genset go..you are on the hook. If your boat has a lot of similar boats available and a newer model has come on the scene ...staying on the dock gets expensive.
Go into it with your eyes wide open and thinking 5 years down the road. It worked out pretty well for us except the last few years we were not able to use the boat much. We decided it was too expensive to keep the charter boat privately with all its systems and storage..and got a day boat to use, good luck .
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