As a result, this isn’t the kind of market that attracts top-tier PM talent.Your best solution might be to either:1.Take on self-management if possible (and if you’re willing to put in the time/effort).2.Find an individual you can trust to handle these properties, set up very specific instructions and processes, micro-manage them initially to ensure standards are met, and compensate them well to make it worth their while.This approach requires more oversight on your part but can yield better results in markets like this.

Not an easy thing, but saving 20% or more on the cost of a new home seems well worth the time and effort if you ask me.

For what it's worth, I tried to run your numbers using the proforma I use with my CFO clients and I'm getting an IRR (average annual return) of nearly 23% (see page 2): Kalamazoo Properties

Remember there are 4 ways you are getting ahead by owning a small multifamily property (houeshacking initially).1.  

If he's a good guy, he'll tell you if it's worth considering or not!

Some lenders allow exceptions for transfers to LLCs owned by the borrower, but it’s worth confirming first.Explore transfer tax exemptions: Chicago doesn’t make this easy, but there may be exemptions or reductions for certain types of ownership transfers.

Overall closing out 10 months with Pricelabs I think it is worth it, but I still spend about the same amount of time adjusting rates everyday (10 to 15 minutes for 9 properties).

Now, this tenant is saying that they don't remember any agreement and thought they paid month to month and could leave whenever.

Can anyone give me advice on how to go about it if it's worth it?

It's worth a conversation.IF you determine that selling is the way to go, $1M could buy you a comparable property in Scottsdale, depending on where in Scottsdale you'd like to be, and how much land you want on your lot.