Navigating these kinds of challenges can be especially tought when you're just starting out as a landlord.From what you've described, it seems you've gone above and beyond to accommodate your tenant's needs.

Challenges?

I've also heard anecdotally on BiggerPockets that the concept of other States being super landlord friendly is sometimes overblown (in other words, sometimes even in the most landlord friendly states, things can get sticky)In other words, I'm not sure how much the potentially friendlier landlord laws would convince me to purchase far away in other state, when that also comes with its own challenges (the inability to self manage, property management fees, etc) This debate on whether I should locally invest vs out of state has left me wasting time so now I feel I just have to make a decision and go for it. 1.

The dashboard does a solid job of giving a clear financial overview, and even when things get rocky, the customer support team has been proactive.However, Stessa has its challenges.

Challenges?

May I ask what your challenges are in the Midwest that you aren't experiencing in Utah?

I am going to challenge them on emd request with a property management company.

You might join as an investor, but I know I am also being challenged to grow as a business owner constantly. 

Finding a turn-key or new construction unit that is cash-flow positive in the first year can be challenging.

Challenges?