Since you’re considering converting the upper unit into a short-term rental, you may also want to implement strict rules around smoking or strong odors in your house rules to avoid future issues.

Generally larger commercial properties and shopping centers are easier to classify with hard and fast rules, but to the points above the residential areas really move very quickly and have way more nuance than most people care to admit.zip codes are generally way too large for my liking at least in my market to provide any kind of insights other than macro level economics but even then highways or rivers that cut through a zip code can end up with totally different trade areas.we can get pretty granular with cellphone data and with grocery center data to understand the trade areas and their true boundaries, but that kind of data pull is generally only cost effective for investors doing larger scale projects or developments, and honestly we still just end up getting on the ground and feeling it out, so I generally tell people that the money is better spent on a plane ticket and weekend trip in the area you are looking rather than any kind of "trade area" level data studies.and generally B class in 1 area means something different than another. 

There are rules to follow!

I made it a solid rule - no illegals on my jobsites.

Both Fort Lauderdale and Pompano have fairly relaxed STR rules and regulations. 

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?

You’d like to think you get what you pay for; however on this instance you seem to be over paying for hands off passive real estate.If passive real estate is truly what you are searching for, have you considered 1031 exchanging into a DST (Delaware Statutory Trusts) or other rules of syndications?

The season of Bigger Pockets investors posting 10 nearly identical "Looking for a CPA" messages per day.Disclosure: I am one of those people you are looking for.

I know this doesn't crack the 1% rule but because we are putting more than the minimum down we still cashflow.  

The issue I see most is the cashflow gets crushed by HOA fees and the added headaches of having them tweaking rules etc.