Are the waters up north warm enough for a Cat 2, 3 or 4?
No idea. I would assume not in late october.
Not really. The water temp has to be 80 minimum.
That's a major reason that the hurricanes die out as they head north.
The other reason is that going up along the coast cuts off a huge chunk of their fuel, warm water. They can't keep going when there's land nearby. Nothing to fuel them.