While you can't take forever and a day, because a desirable candidate has choices, deciding too quickly can be disasterous.

Trying to balance proper due diligence against my desire to just acquire a bunch of mediocre units!  

Here's some STR companies in the area that can possibly help you out...Go Wander Home Desired StaysThe Sosi

Midtown refers to a specific area and it's quite desirable. 1/1 MTRs would do well here IMO.

If it's just a money grab and there is no desire to associate with the aforementioned, you will most likely be on the losing end and feel very negative about the program.

Repeat as desired.

We are looking to buy a condo in Chicago as the new rental, for a variety of reasons, but most importantly because it would rent better in the city, and it fits our desired price point (so we can allow for the rest of $$ from the sale for paying off their Oregon home and pay all, or some of the taxes on the boot). 

I suspect maximizing the investment might make it slightly less desirable as an owner or at least the renovations might have lower ROI if sold to a homeowner.

For $1,500 renters in Cincy would expend very nice place on a quiet street and desirable area.  

On the other hand, keeping the house could allow us to maintain an appreciating asset in a desirable location.I’d love to hear from others who’ve faced similar decisions.