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Does this sound like a crazy amount of work for a 37 year old boat and 23 year old motor?
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Nope!! Some here have even done more!! I had a 1975, I did not need a transom but i converted it from I/O to outboard and all I ever had on it were 25 year old motors!
I have since sold that boat and have a 1984 23 Sea Ox and it has a 1985 Merc on it.
If you like the boat go for it!