Dave-
I just returned from Sarasota looking at a business to buy and the surrounding area for storage locations for my three boats. When I found out I had to drive to Tampa to sail I broke off the deal. I have three boats and all are for different uses. I would say the deciding factor for me would be "How much time does it take to launch and retreive?". Also How much money are you planning to tie up and/or what else could be done with the cost [money] of boat #2 or #3???
In my profession debt is not a good idea because when the economy is good its really good but when its bad you definitely don't want extra monthly payments...
thom