To get started, you’ll need a good understanding of assigning contracts (check your state’s laws), a solid buyer’s list, and marketing tools to connect with motivated sellers.

Hire a manager; is that similar to a property manager of sort but for senior living?

They have all sorts of problems now. 

Anything over that could mean that the property is overstaffed, or it could mean that management is delivering a very high level of service such as in a luxury property that has a doorman and all sorts of staff that you don't typically see in garden style apartments.

I'm specifically interested in "main street" properties with a downstairs retail space, upstairs apartment(s).If you know of anyone with this sort of experience, I'd REALLY appreciate the connection.

I would have bought rental properties of any sort before I bought my primary home. 

I am thinking two things:  First, do you have a spreadsheet or program of some sort that you can share with me so I can analyze a deal?  

The app doesn't allow rent by room, so I am sort of forcing it.

My motivation is to increase my financial literacy and diversify into real estate.I have rented all my life and seek to become a homeowner/ investor to help my family and make their lives easier.

He's still very much in contact and reachable, but my biggest fear is that he will run or file some sort of Bankruptcy.