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). 

I met with Jeff Kolp from State Farm to talk about something similar.

Find what other similar comparable properties are selling for.

Hope to meet people with similar interests.

Taylor, I'm in a very similar situation as you.

Similar to this:  https://www.behmdesign.com/product/apartment-garag...

If you have a lower gross rental income per bookings (say $150 average booking for a small condo) and a similar $20 cost per basket, but that basket includes nothing that is tied to the identity of the property or makes it unique, it seems likely the repeat booking rate and likelihood of positive review will have minimal impact.

Now, I take full responsibility for my ignorance here and just blindly signing things, especially as someone who deals with commercial finance regularly and has his own clients sign similar fee agreements.Honestly it just never occurred to me mostly because I was just so damn excited to sell the house and be done with it.