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?

Hi Max, a good rule of thumb is to start with your target market/ideal guest.

For suburbs you really have to search for each cities rules.  

In the unlikely event that you are the exception that proves the rule, the rare 18 year old who can actually generate a serious income by wholesaling real estate, your day to day will look like the following: - You will door knock, cold call, send mailers, and otherwise create lists of people who are in the most desperate moments of their lives. 

With the economy of scale in multifamily, each additional unit nets you a little more than the last, as a rule of thumb.

Since you missed the 2 out of 5 rule, capital gains taxes might take a chunk of your profits, so consulting a CPA would be smart to understand how much you’d actually keep.

I would apply the cash flow to pay down the debt and hope to have significant passive income (or equity to put into something else) in 10 years.

But you also have to apply your level of risk aversion or risk adjusted return.  

Esprit if it's causing issues with other (good) tenants and they aren't following the rules of the lease I wouldn't renew.

Late Payment Penalty: A late payment fee of 5% of the overdue amount will apply if payments are more than 10 days late.3.