Most Heloc rates right now are around 7.75% to 10% so if you look at your blended rate between your fist and Heloc you would be better off doing a cash out refinance.A lot of people forget or simply do not know that if you do a cash out refinance the rate does go up but in 12 to 24 months if you do a "rate and term" refinance you can get it back down fairly close to where it was at prior.

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

Assuming it simply won't happen, is failure to plan.

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?

God bless you both.