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 are (older/retired) and could benefit from house hacking and buying a duplex, or renting a room.

He’s only 55, he can enjoy his retirement, golf, etc for a few years and buy back in when he sees a good opportunity.

Absolutely, the passive income from owning rentals is great but I also love getting into big projects and seeing the transformation from start to finish@David Jesperson What city/market are you looking to buy and what type of properties are you looking for, SF, 2-4 MF, or 5+ MF?

You can get started with rent to own/lease option or another creative strategy like buying subject to. 

So to answer your question, I don't think buying the cash buyer data feed is necessary. 

I purchased this before deciding to get in to real estate.I am trying to decide if I should rent the property out or sale it to buy something with long term investment in mind.

The Retainer Fee is credited towards whatever they buy from us in the 90 days, so in effect, costs them nothing.Note: we're not doing this to make money, but to avoid the time-wasters.

Quote from @Donald Hatter: Investment Info:Single-family residence buy & hold investment.

This means that you will probably need to pay registration and filing fees in at least 2 states if you don’t buy CA property as a CA resident.Be sure to tell your accountant that you may now need to file non-resident income tax returns in each state where you own property as well.