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Thanks everyone for your input. I am on the east end of Long Island (North Fork) and the boat would occasionally be used to visit friends in Montauk. We also have family that we would want to visit on Block.

If there is one thing that I remember about the Montauk was the way the boat pounded. We had it out in New York harbor one day and it was hell. There was one time I remember the front hatch came off.

The cost to repower is my all in cost for an OMC (rigging, controls, getting rid of the old engine, etc). it's actually $11,700. I cant find any dealer on Long Island any cheaper. Although my brother's boat's hull is in nice shape, all of the teak, seat cushions and electronics need to be replaced. I am thinking that that is going to cost me another 2-3k.

I am also a little worried about the capacity of the Montauk. It only holds 7 people. If my wife and I wanted to take another family out we would be over the limit (with kids).

Despite the emotional attachment to the Montauk, I think that I might look for an Outrage 20 or maybe even a 22. Seems like for not much more money we are getting a lot more boat.