1) All Cherubini Hunters were built basically the same, which is to say they were solidly built but also built to a price. The consensus is that the Cherubini Hunters were the best built Hunters. What I have noticed with my 27 is, there is a lot of decently put together stuff, and some areas that need improvement.
2) The hull is solid glass. The hull to deck joint is an L shaped aluminum toe rail, a layer of butyl tape, deck, another layer of butyl tape, and an inward turned flange, bolted every 4". It's likely the same in the 36 but not positive. I have not noticed leaks from mine, everything else leaks, but not the hull-deck joint.
3) No way can this boat be powered by a small outboard, you need 10hp at least to be able to control a boat that size unless you motor around in calm conditions. Sculling it? Maybe with 3 people on each side.
4) absolutely, if it's sound, it's perfectly capable of going to the Bahamas.
5) absolutely, if it's setup for it. They came from the factory that way, stuff may need to be updated of course.
Here is a better place for info on Cherubini Hunters...
The Cherubini Hunters - SailboatOwners.com