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I did it.
I bought a used boat, coming out of the Sunsail fleet. Then I placed it in charter in a "second tier" company in the BVI for 5 more years. I agree with everyone's comments about wear & tear, stuff getting lost.
That being said, the costs, when you include the tax advantages, came out fairly even over the years...that is to say I almost made enough to cover the costs, but then I enjoyed the pride of ownership and I knew the boat alot better when coming down for my vacations. I also got to keep a couple boxes of gear and toys down there to use on my trips without having to haul it back and forth.
The biggest advantages were being able to go where I wanted with the boat...the charter companies put some tight restrictions on their charter boats, but as an owner we could explore alot of places the charterers dont go. Also it was nice to have someone else taking care of all the maintenance stuff for me...I could enjoy my time on the boat without having to spend my week off changing oil and scrubbing the bottom.
Chartering will allow you to afford a bigger boat then you otherwise might have...but you have to accept that there will be alot of wear and tear in trade.
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