He believes he can find all that he needs to know on the internet.

From my understanding, no one is employed, they are somehow current with the rent, but they are definitely not someone I would offer a new lease...not even at market rate.  

Being NYS, you've got to know Landlord/Tenant law or leverage someone who does.

I know they are legit because I listed my property there and it got rented by someone looking to do Airbnb.

I'd recommend talking to local investors of your prospective cities to get positive and negative feedback, someone who isn't trying to sell you anything.Do you mind sharing how much capital you have to invest in?  

If the contractor is changing gears I would find someone else.

As someone else said, check the history of prior gas bills and the average bill in your zip code, and understand that you might have to eat that cost.

You can find qualified buyers that are small business owners, tradesmen, etc just have someone qualified to do prop underwriting be fore you sign the agreement. 

People house hacking have far different expectations than someone buying properties with cash. 

Instead of paying down someone else’s mortgage, you’re setting yourself up for bigger and better deals down the road.Your first deal is going to depend on a lot of factors—how important is location?