My goal is to purchase a duplex in a solid A/B neighborhood to operate as a mid-term rental (MTR).I know how important it is to have the right team, so I’d love to connect with investor-friendly real estate agents, property managers, and co-hosts in either market.

You can search for The Investors Guide to Memphis Real Estate anywhere you listen to podcats and you can watch it on YouTube. 

Even my own JP at 25,000 people has at least 4 very different neighborhoods off the top of my head.

That name is on VRBO, so guests can then do their own Google search for the cabin, and voila! 

I am not sure either Chicago neighborhood is better than the other...I just think that the longer-term upside is higher and will happen with a bit more vertical line-up in appreciation.  

I am always hesitant on build to rent neighborhoods. 

Since you're new to the market, I agree that working with an IFA will help you tremendously, especially navigating numbers, neighborhoods, and strategy.

“unrelated to the various bugs, the search function would be poor for 2005

Or keep searching?

Cities that do not rely on visitors often see STRs as a threat to housing or neighborhood stability.