@Derek BrickleyYou're correct when it comes to financing.

Than maybe with adjusting the vocabulary to REALIZED performance and UNREALIZED performance, we can start correcting understandings. 

I’m all ears for any guidance, recommended reads, or war stories from those who’ve been down this path.

What do you do to ensure that the tenant is responsible for security deposit disputes since that is the largest reason for owner lawsuitsHow familiar are you with the newly changed laws that can affect you the owner if they are not used correctly?

Going down the path of house hacking would be the advice that I would give anyone in your position.  

* What do you do to ensure that the tenant is responsible for security deposit disputes since that is the largest reason for owner lawsuits* How familiar are you with the newly changed laws that can affect you the owner if they are not used correctly?

Quote from @Joe Villeneuve: Quote from @James Hamling: @Victor Tofilski I can't tell you exactly why it hasn't leased yet but I can pick it apart and give you detailed road map of every deficiency I notice and how to correct. 

I own an HOA management company in Hoboken and it's led me down this thinking-path as well.

It is a lofty goal with no easy path to accomplishment, but what you describe seems unlikely to accomplish the goal.Note most people on this site are RE investors.  

Please correct me if I'm wrong.You can require them to have insurance, but you cannot require them to purchase from a specific policy provider.