If this is your only rental, it's more about if you want to keep the property from a management perspective.

What's your biggest time management challenge?

I'm considering partnering with a non-profit that would manage the sober-living program; with me just providing the house passively for rent on a per bed basis. 

We manage a property that was having drain field issues for awhile, got estimates and had the owner approve one of the vendors.

It is surprisingly easy to manage out of state and if you want more tips on how, check out Bigger Pockets book "30 Day Stay" on Mid Term Rentals. 

Since your goal is getting into commercial real estate, it might make sense to start with a smaller rental property like a duplex to get experience managing an investment.

The same is true with property management.

Property Manager – This is another one I really need help from the bigger pockets community in the local area.

This also leads owners to ASSUME simpler is better when it comes to management contracts.

I get it with the builders.. we saw that big time in the GFC however the deals I saw was them walking away from substantial EM deposits deep into the 6 figure range.. we did well picking up some lots from lot developers who had this happen to them..