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I think your biggest determinant now is to decide how much you are going to use the boat and how much family, work, etc. will get in the way. I think most people think they are going to use their boat x times and their est. is off (as it is/was with my little boat). Maybe do it for 1 - 2 years and see how what you learned out of the process. Did you go out x times per week, did you enjoy a certain boat/style (cuddy, CC, etc), etc.
After that 1 - 2 years you can make a decision - what will you have lost over that period? It will cost you the amount of the membership/dues but I bet it won't be much more than the amount of depreciation/expenses if you actually bought a boat.
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