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Around here (mid-Atlantic) it seems like the majority of Montauks have no bottom paint. They seem to be more likely to have been trailered/garaged than some of the larger models. So hereabouts a no-bottom-paint Montauk, while preferable, is not necessarily a stand-out.

As for that engine -- there's no telling really. It could last many many more seasons, or it could fail catastrophically on your first excursion. So there is some gamble there. Having it inspected by a reputable engine mechanic prior to purchase could give you a better sense of its condition.

Overall, I would say that his asking price is pretty rich. Or maybe they are worth a lot more where you live? But you can take a look on your local Craigslists to see what others are asking. An important thing to remember is that those asking prices rarely hold up in the final negotiation. Most sell for significantly less. Another thing to know is that properly-priced items sell quickly and disappear from the list often within a day or even hours of being posted. So you tend not to see them and are more likely to be seeing ads that languish because they are priced above what the market will bear.