The 5-10 it gets heavier and a lot busier, and 10-15-20 it really is untenable to self-manage especially if this is not you main business like a person buying their own rentals and building it like a small business. 

Quote from @Mitch Seiffert: I have a single-family house in Minneapolis that I've been approached by a couple of parties interested in using it as a group home.

I will reach out to you personally, please keep an eye out in your inbox.

Typically someone who was communicative turns distant, unresponsive, blows you off when you're trying to talk to them in person, and the tall tale sign of boxes in the hallway.

Housing has become a "crisis" all over the globe. 

@Greg Scott thanks for the mention:)@Usman Khan welcome to the "fun" of S8, where you can rarely get ahold of anyone at a Housing Commission office:( THey are all overworked and underpaid.Reference this for your S8 training and maintenance:https://dhcmi.org/sites/default/files/upload/LandlordGuideBo...

Personally, I like to use Notion for this type of task, but I'm sure there will be others on here that will recommend Monday.com, ClickUp, or Asana.

Who is personally going to be liable if the guarantees aren't met?

I personally target Lauderdale, Limestone, Morgan, and Madison Counties.

If multifamily interests you, you might want to consider house hacking as a low risk strategy to start.