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The Classic 15s ride great...and like you said are super easy to handle, trailer, etc.

But, the seating isn't the most comfortable in the world, and I suspect it gets worse as you get older. I suspect you may end up regretting the trade down the road...

I love my 15' Super Sport, but ended up buying an additional, bigger boat for the comfort factor.

Perhaps there could be some benefits to you trading to any era 17 Montauk or even a new 150 Montauk... But I'm with the rest of the posters...figure out how to make your current boat easier to deal with....perhaps a new, properly fitted trailer (though I see you are in Cali, where new boats are more affordable than new trailers)....or a new jack stand (I'm not sure why you are lifting the tongue anyways).