At the beginning of every winter season, I send a message to the tenants with the account information and let them know to call the gas company if the heat goes out.  

Tread lightly there as NY/NYC is a market for seasoned investors so you need to be able to see some of the schemes the buyers (and agents) will try to pull on you early on (too many to list).

For whatever it is worth, we rent our STR by the month during the non-tourist season and we have a walk-through video on YouTube.

Old town is more of an older crowd but Del ray, and several other areas around old town might find better tenants who will want to rent by the room.

Someone experienced and seasoned, who can hear my plans and goals and give their take on how to reach them, or offer new ideas. 

I understand the intent behind the law, but most investors will find ways around the law, or just opt out.This is a question for a seasoned attorney in the market.

The owner is an older gentleman and has managed this property for years.

Try searching for older single family houses with a mother-in-law suite or guest house.

They have a ton of equity >$100K, <3%, but older home in need of roof, A/C, and water heater in next 5-10 years.

Older homes have more problems.