One investor might think its a good fit for them and their situation while another investor won't. 

There are a lot of options, but try to make a list of three things you think the town needs that it doesn't have right near there and that may point you in the right direction by talking to someone at the town office.

Echoing what Shawn said above, you would have a vast array of options ranging from lively resorts with tons of amenities (think water slides, lazy rivers, tennis)...ranging to quieter resorts with lots of green space and forest or lake view homes.

What do you think are the potential benefits and drawbacks?

Both will have their pros and cons...also I think you have to consider your tenant's expectations and the price point you are going to be renting at?

Then there is an entrance from the back that leads you into the kitchen, plus you can enter from the main entrance in the front that has stairs that lead you to the other end of the apartment.Yes, you make valid points; it might never happen but you never know what could happen in the future, so it's something I also need to think about.My previous tenant that was living there, was there for 20+ years and never had a complaint about the heating/cooling with her; so hopefully this continues with the next tenant. 

The disadvantage of living in NYC is that the prices of homes here are high.The advantage is that our salary is higher than other areas.I think you should consider to continue living in NYC and invest in out of state rentals.The only exception would be, if you can work remote and keep your NYC salary, then I would consider a house-hack elsewhere.

Why do you think purchase contracts are so long and have such small print?

I think its more of a business and life lesson honestly... become a master of your craft, and everything else becomes much much easier.

I'm thinking the fence can still holds but may need to be replaced in the future.