I’d recommend listening to the straight up Chicago investor podcast for local information, going to the variety of meetups that are in this great city, and meeting a lot of the people posting here. 

ways to meet such people would be meetups, or simply walking into some smaller offices, could also ask around to other owners of the assets you are interested in and see who helps them. 

Looking forward to meeting likeminded people :) 

We are seeing about 50/50 split of people holding as rentals vs selling. 

For example, in my state PA there is an inheritance tax and many TAX auction properties originate from people passing away and the heir(s) not taking control over the estate and paying those property taxes.

In the “old” days, people would have the seller pay the lender so as to not “alert” the lender that a property sale had taken place, so that the lender def wouldn’t trigger the so called “due on sale” that’s a part of almost every mortgage or deed of trust document.  

The credit committee is usually made up of local people who are familiar with the market they are in.

They likely know people in the area, and then they might feel that you are trying all avenues to find the next tenant.

That’s the stuff people gloss over in spreadsheets but makes a real difference in how smoothly a project runs.

Otherwise perhaps your winter people will pay $500 extra if your cap is $500 and that is not what your competitors will be doing.