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They are ALL money pits. Today, everything is a money pit. But to me, fixing stuff is FUN; and fun is worth money! If you don’t want to spend money, really the only solution is to sit still in your living room. Not an option, for most of us. I would say that a ’58 Big Twin is less of a money pit than say, a Mark 58 Merc; but that is a general statement. It totally, TOTALLY depends on how well the motor was taken care of, before you bought it. Let me ask you, why do you want it? If you want it for eye candy and an occasional run, fine. If you want to go fishing with it regularly, it is going to use quite a bit of fuel, compared to a modern outboard. In that respect, it would be a money pit, for sure. I think you will find that normal maintenance parts availability for the Big Twins is quite excellent, given how old they are.
Long live American manufacturing!