My wife's full-time job is raising our children, but her side hustle is managing the day to day operations of the Airbnb, so we have a unique situation that would allow us replicate this model in the future :). 

There are specific regions of the country I'm eyeballing, but they are broad swaths (PacWest, Great Lakes, etc.).I need to narrow it down to specific cities.What are your tips for how to evaluate, from afar, the right OOS cities for investment?

It is difficult to figure out what is going on in your post.If I understand correctly: that you have a property management business (LLC 1) and you recently bought a commercial property under a separate LLC (LLC 2) and that you want a rental agreement between the two LLCs.Just make it arms-length and fair market to avoid problems.If both LLCs are disregarded for federal income tax purposes, the lease will also be disregarded and won't be respected for federal income tax purposes.If the management LLC is an S Corp, you'll have a self-rental situation that has unique passive activity loss rules.Your professional advisors can fill you in on the details.

As you know, HML's aren't like banks, that have various loan programs that are offered by many other banks, but each is unique, with varying conditions.

If you are interested, I can connect you with the regional for EVOLVE so you can find out more.There are a LOT of factors to consider with a property in this area.Is it within a city's limits?

By having access to over 40 lenders (including major banks/institutions), we're able to compare options and choose the ideal lender and interest rate for each client's unique goals. 

In about 1998 when I was about 34 I made my way to the world of corporate Convenience Store / Retail Gasoline management with a large regional chain here in FL.

I am looking for a good regional or small bank or credit union that offers good terms and products for investors in Michigan.

If there's something unique about the house, give that information..

I made a trip to Chicago in college to tour its architecture, because the styles are so unique, given the fire, Frank Lloyd Wright and a few other reasons.