Look at sales of nearby similar properties. 

You can get similar $$ in Big Bear Lake without the issues of Lake Tahoe.

The National Association of Realtors is a good resource for info like this.https://www.nar.realtor/research-and-statisticsHere is a similar link from Zillow.https://www.zillow.com/research/data/

If I bought a house at $25k, I think *all* houses should be able to be had at $25k, or thereabouts - so I tell myself I just need to 'wait for the right deal', or 'work the margins harder', or something similar.

My strategy is similar to most as I try to get the borrower performing again.

Thanks John Leavelle funny because i had actually asked a similar question a while back and someone told me to reduce those numbers you listed because of the rent amount in my area (i had them all in the same place last time).

What kind of similar steps should/could we take to vet a property manager co?

If the price for this property is similar to some other Indiana prices I've seen, the issue could be your reserves, meaning the lender wants you to have more of a rainy day fund. 

I’m wondering if other Chicagoland investors are at a similar place of considering cashing out.

If you have a cheap rental and want a basic kit, you can get similar closet kits from Walmart.com (ship to store for pickup).