Secondcurve, you are way too conservative on the taxes & condo fee in your example. Both would actually be much higher. On a slip assessed at $69k, for taxes to be $500, the per thousand rate would have to be $6-$7 which we all know is way too low. The rate in Gilford is $17-$18 per thousand so that would be $1173-$1242 in taxes. I don't know about other condo marinas but MVYC is $1200 per annual dues(condo fee).
If I were in the market now for a slip I would have to put serious thought in to it also but I was fortunate enough to buy a few years ago. My slip has appreciated 3-4 times what it was when I bought it. Even with the taxes being higher & the condo fee I still could not rent my slip for less than what it costs me to own it.
Even though I own a slip I would like prices to come down. I would like them to come back down to what I paid. My taxes would be much lower & I did not buy for investment. I don't intend to sell it, I bought it to use it.
The one good thing about buying is you have equity that you don't have when renting. If you know you will be boating for the next 20-30 years building equity by buying is better than renting. In your example if you rented at MVYC for the next 20-30 years at $4k per year (which is low, many go for more) that would amount to $80k-$120k with nothing to show for it & you could have bought for $69k. If you were only going to be boating for say 5 years it would not be worth it to buy unless the value appreciated enough to make a profit.
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