I always run my numbers on WCS (worst case scenario), but in today's market you leave SO MUCH on the table with that mentality. 

Worst case, don't renew his lease. 

A ton of great advice in here - very helpful as I get started.I am going to move forward with the assumption that I am going to manage at least the first 2-4 units, but continue running the analysis both with and without a PM to understand best and worst case cash flow scenarios.

@Kevin PerksInstead of formulating whether you should do something or not, you should be talking with professionals telling them what you are looking to achieve and ask for their advice on how to achieve that.I talk with so many investors who go blindly into establishing an LLC who have it set up incorrectly.The worst part of having an LLC set up incorrectly is that you think you are getting liability protection...when you likely don't.Best to talk with an attorney on asset protection / LLC Formation.

Should I have some sort of online application as well? 

He had no family but a close friend who visited often holds the estate, is it wrong or tacky to send some sort of something to let him know I’m available.

To me, a worst case scenario is if I realize in three years that my analysis was incorrect and I will not get positive cash flow. 

Leaping to a very dark place, in a worst case scenario your only option might be to threaten to sell your interest to someone she hates. 

I saw the worst part of humanity, very depressing.

Remember, I am using my worst appreciating property.