We are purchasing 1.39 acres of land and plan to utilize a workforce housing ordinance through the county to reduce the required lot size to fit more houses onto the land. 

@Henry Lazerow  The neighborhoods of Chicago don't fit nicely into an A to F class system. 

its horrible. no one answers the phone. they promise an easy refund if the lead never answers after 21 days, if the number is wrong/ doesn't ring/ among other reasons you can find in their refund policy.however, they will deny you when you try and get your refund. i had one lead where the number doesn't even ring, and another where the person never answered within the timeframe. they denied my request for a refund, although it completely fit their refund policy. i believe less than 8% of refunds requested are ever refunded. horrible experience.

@Mohamed F., it depends on how you measure it?

While STRs in touristy spots might not seem like a fit for LTRs, I’ve found a sweet spot with mid-term rentals in the off-season.

The way to gain 100% financing for purchase & rehab is to get your purchase & rehab numbers to fit within 65%-70% of the ARV (not easy, but possible).

Building an ADU to fit all 3 of you might end up being more than $250k.

Thank you,Denise Agree with Jay, if it does not sell for what they want goes back to the bank and then the bank can deal with the sale at a lower price or whatever they see fit. 

What information should I provide so a possible investor can make a quick decision on whether it would fit in their guardrails?

Dayton/Centerville could be a good starting point given your familiarity and existing connections there.Here are a few steps to consider:Explore Cash Purchases or Lower Financing Options: Given that you're considering not using financing, you could look for properties that fit within your budget for a cash purchase.