Also @Tim Phillips something to be aware of in FL, all condos older than 30 years and taller than 3 stories are required to have a "Structural Integrity Reserve Study" performed before the end of this year.

I guide clients who are looking to treat their STR as active.Somethings to consider are whether you should get a cost segregation study done, creating a log of your hours and having an understanding of what hours count / don't count.

I realize that a full feasibility study will most likely be required if I move forward with an LOI and purchase contract.

Although not classically thought of as Midwestern have you also thought of Tennessee and North Carolina?

I'm one of the case studies in the BP book, The House Hacking Strategy. 

Aloha,For comparing Condos/HOA projects for investment purposes, the more critical info would be rating the most recent Reserve Study and/or Reserve Funding Plan for a specific project.

You are asking the classic question in the MTR space: how does one evaluate what could be a good MTR.Unfortunately, MTRs are at a point similar to where STRs where 10-12 years ago, and there really isn't a one stop shop source for great data.

There was a case study where a GP raised a million dollars for a deal with 70% of the funds coming from his personal network. 

Associations must now conduct a Structural Integrity Reserve Study (SIRS) to ensure they have adequate funds for necessary repairs and maintenance.

Document your experience so you can share a case study here or at your local REIA