Or is your concern about cash flow related to your lender?

Finding a good PM will cover your concerns on managing the rental from OOS and a good agent should be able to provide you with their network of deals, including on and off market opportunities. 

In fact, your feeling overwhelmed is because you don't know how to solve the issues that concern you YET. 

We are in a safe community, so tenants can choose to leave the door unlocked or hide a key under the mat.

These 2 platforms don't focus on MTR but vacation rentals so using Furnished Finder is a better way to get those longer term folks.I have always been a bit concerned about the area's penchant for restrictions.

If the tenants don’t leave by the deadline, your next step would be to check your state’s landlord-tenant laws to understand the eviction process.

Maybe look for a different type of tenant that doesn't leave every year or sell the place if it isn't meeting your other investment objectives.2) As PM's we always seek prior authorization for expensive turns or capital projects, even though the estimates given to our owner-clients are often ball-park numbers.

There is a fine line between offering a well rounded service and leaving too much in the home.I love the business and glad to be a Superhost but this has been my experience.  

If you can't leave NY, I really wouldn't try to do a BRRR from that far away unless you have someone you trust who is local.

The deal will leave the seller at your sons mercy for decades (the life of the loan).