If you find a good manager, you can still make as much money (or more) because they will attract better tenants at higher prices, reduce turnover, maintain the property better, reduce losses from amateurish mistakes, etc.3.

Your best bet from what you said, for proximity and ease of use and volume of vacationers would like be in the Woodstock area or the Catskills.

Rather than second-guessing "what is the new hot STR market" as I see many do - I may be biased - I believe it makes more sense to invest the time in figuring out how to succeed in a year-round market which is proven to attract tourists year after year.

There's are four founders and they're all incredible people & attract a great group.https://www.eventbrite.com/e/503432118017 (https://www.eventbrite.com/e/503432118017)The Elite Investor is one I've been wanting to go to however have not made time to.

Are there any big companies or industries close by that will attract tenants to this area?

You want to look in a market that has legal approval for short-term rental and draws visitors (are there reasons to visit such as attractions, nearby cities, outdoor life, lake, beach, mountains, etc?).

Again I've never installed one, I have no idea how much they cost, its just something that makes sense to me as a feature to attract top ocupants.

Big amount of square footage in a high cost area. 3/3 made it attractive as a starter house.

Blue Ridge looks attractive based off my search and pricing there. 

as has somewhat been brought up already, if the building only has a year left on the lease term thats much less attractive than 25 years.