They know every painter that comes in there to shop and can makes recommendations.Also,try the local paint stores like Sherman Williams and others to see which painters shop there.I bet the salesman have family members who are painters or know who the best painters are around there.

If you are betting on appreciation, that swings the equation towards buying another house.

Seeing as the area is known for getting away from it all to the country, I would suspect a more secluded location would do just fine.Best bet would be to look at other rentals in the immediate area to see what they are charging for nightly rate, what their calendars look like and what amenities the offer.

Your best bet if finding the floor plan for the home and marking it up with notes of what type of work you want done and then asking contractors for several bid proposals.

And you're not doing the thing where you accept negative cashflow while waiting/betting/praying on appreciation, because you've got to live somewhere regardless. 

I'd bet saving the time is the better option.

I would bet there is no insulation in the walls and a lot of the cells will be grouted full. 

I bet somebody will make that home incredible.  

IDK banks policies but someone local is probably your best bet.

But, if you attend a Brooklyn, Manhattan or Queens REIA I bet you'll at least get some support from experienced local investors.