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?

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

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

That's a fundamental requirement.

The interior is decent and also requires updating .

Without rent control i either raise their rent far above market rents so they give me notice (my preferred method) or i simply do not renew their lease.

Tons of double sided tape used which results in a fair amount of extra effort to restore (most cases paint comes right off the wall requiring patching sanding etc, some cases Good-off was effective.

It requires registration, so there could be some fees or work involved in setting up.

If you want to know if it is a fair price for your area and this time of the year, simply get two or three more bids.

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.