Seems that as long as I build the cost into my numbers up front it'd be a good way to limit my exposure to tenant struggles and take advantage of the company's experience and knowledge of the market.

Looking to explore options for owner occupant lenders outside the conventional limits that borrow in Chicago to high credit/income individuals with under 20% down.

As far as the Umbrella policy goes you should look at an Umbrella Policy as "excess liability" or "secondary coverage" meaning the underlying policy (home or auto) pays first in a claim situation and if the claim exceeds the limits of the underlying policy THEN the Umbrella kicks in.There are companies that will sell you an Umbrella policy without requiring you to buy another policy from them ...but...they still want to verify your underlying coverage on the home and autos.Geico is an Auto insurance company first - they broker out the homeowners policy to other companies which is why you may not be getting good advice from them...plus it's an 800# and the kid you are talking to may not have any real world experience in what you are trying to do so can't think of any solutions.Try reaching out to a local independent agent or a Farmers agent - Farmers has options to put all but one of your autos in "storage mode", and should be able to combo that with your home as a landlord policy thru Foremost then set up an Umbrella policy for you on the entire package.

(which he did not)  She is having a good look around so I ask if she is hard of hearing and tell her she left the place in a disgusting state after she was trusted to rent with animals and that I really didn't want her in there.15 mins later, I follow her out back, behind the property and she is now on the god damn roof (stable block with is unsupported and poss rotten) as she needs to get her wind chimes she left.I ask her to get down as that would be my liability and (also ask if she is a grown woman or a child so lost my cool a little) agree to climb out the window to get the darn wind chimes.

I think that the other way to go is to keep deferring your tax liability by continuing your 1031 filing. 

Figure 10% higher tax (cap gains vs ordinary) and SE tax isn't too bad If someone is over the Social Security limit however still sucks paying it. 

Because FCRA specifically forbids someone from waiving their rights to protect the information.There are some very limited exceptions.

Directly from Allregs  Fannie Mae's guides:Limits on the Number of Financed PropertiesIf the mortgage loan being delivered to Fannie Mae is secured by the borrower’s principal residence, there are no limitations on the number of other properties that the borrower will have financed.

They include (but not limited to) any loan mortgage payments, taxes, insurance, utilities, HOA fees, etc that occurs during the Rehab period and up until the property is fully rented.  

But also consider the legal limitations/costs in each market.