An agent will want to see your prequal before writing offers.

Today, I have maybe 3 that I work with and they have there ducks in a row - updated POF (not 3 months old), they let me write clean offers, they are all-cash, and they shortened their contingencies and they follow through on the purchase and then re-list with me.

Also, keep in mind, there are great benefits as an investor of income properties, you can write off, depreciation costs, and if, it doesn't rent, you write that off as well.

I figured I have been very busy and haven’t been writing.

There are many A rated carriers that write coverage in the South burbs of Chicago.

(we'd write a dog security deposit equal to that cost into the lease.)

Under new tax law you can only write off your first 500k in interest on the mortgage anyways as of right now.

I was hoping I can gain some insight on some possible strategies "to bring my talents to south beach" - Lebron James.

They write a stand alone umbrella that should cover over both the homeowners and the rentals. 

Definitely document everything in writing and have her sign it all, not the people you are buying the place from.