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Are there rules about renting it out?

Fortunately the rules have been "modernized," which is kind of a rich NLP technique if you ask me. 

Purchase price: $160,000 Cash invested: $35,000 Purchased this property as a turnkey investment at the 1% rule moving equity from another deal.

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?

No, ok, rule in your favor.

The most important rule is to have the cash flow of the new property be able to pay all its expenses, mortgage, AND the line of credit back.

I wouldn't rule out a duplex as we have far more duplex properties than quadplexes.

You can still easily find the 1% rule and positive cash flow and there's amazing appreciation potential.

Hey @Joel Oh, so let's clarify the NYC rules around STRs.STRs are legal in NYC as long as these directions are followed."