Often I can smell scents from the lower unit that aren't pleasant (cooking, smoking, etc).

Should I make an offer with the qualification that all furnishings, dishes, pots, and pans stay, except for "personal" effects?

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?

I agree with the comments above.Most important is a fully furnished, comfortable property with the basic amenities: coffee, teas, functional kitchen (all utensils, spices, cooking and baking, etc.)

Ergo I do all the cooking and cleaning  LOL It doesn't hurt that your wife has a client (you) that gives her all his new builds to sell, lol. 

Quote from @Matthew Cook: Dig into those comps with a realtor doing business in that market.

Quote from @Tod DuBois: Another Furnished Finder POT cancelled on me after I went out of my way and paid to review them on Key Check and signed up for Key Check contracts, made two contracts, allowed a pet and still, two days before the check-in, they did not sign.

You want to know where you stand before jumping in the pot. 

But if I'm going somewhere with my wife for any length of time, I like the space afforded us by a vacation rental, the kitchen for cooking, a living room for spreading out.

Less licensees paying into the pot means everyone's costs go up.