I owned a boat in charter with the Moorings/Footloose for 7 years and have no regrets. For me, it basically meant I could use my boat or boat elsewhere for 5 weeks a year for what chartering for 2 weeks would have cost.
A few more specific thoughts:
I much prefer the guaranteed income option. I've hard stories about people who have commission contracts but their boat doesn't get charred out nearly as much as they were lead to believe.
Talk to your tax person about the tax consequences of earning income and writing off depreciation on the boat. This is something I find the charter management companies tend to gloss over.
Make a rational economic comparison to what you would otherwise realistically do. Charter management is likely much cheaper than buying
the same boat and using it of the same time and likely cheaper than chartering the same boat 5 weeks a year, but is that what you would actually otherwise do? With my charter boat, that was absolutely the case, but as I now look at Cats in charter management, I realize that buying
a used one at 25% or the cost of splitting a few charters with friends is more economical. When comparing buying to chartering be sure to consider the cost of your money
(lost interest) or interest on a loan. By dumb luck I bought my boat just before the 2008 crash, so it ended up being an even better financial decision.
Think about what will happen when it comes out of charter. A year of storage
in the VIs could easily eat up a huge chunk of that savings.