On Zillow, we simply call it #A with the same address.

If they default, you keep deposit and anything they have paid prior to default and simply evict them.

Quote from @Collin Hays: I suspect that the Smokies is your best choice, simply because it is a year-round destination. 

Should it simply be one of two choices: deny application or accept application with ESA exemption even if the property qualifies for the FHA exemption?

They simply do Fannie, Freddie, FHA, VA, and USDA loans.

In my experience, it is worth simply reaching out to your realtor first. 

If this is simply you not wanting to accept partial payments and the rent is current, stop accepting it - and send a Lease Violation/Notice of Quit for Non-Payment of Rent - and force the full rent to be paid per the lease or start eviction.  

Given that I'm not positioned to buy just yet, and simply running the numbers, is there a rule of thumb for estimating insurance costs that would make sense in Cook County?

Sometimes emails go to spam and simply some people just don't check their email religiously like the rest of us.

I think it’s a more recent consideration (maybe in the past decade or so based on my digging / anecdotal feedback) and perhaps some of you that have been in the business longer and simply renewing old policies may be getting a pass.