There is loads of opportunity in the Chicagoland area from low to high risk so what ever your appetite is there is options here.

My biggest problems right now are a picky "high maintenance" couple and a couple with a toddler who are excessively colonizing the hallway outside their doorway with strollers and other junk.

Sounds like it will pay off in three years.I shoot for $450 a month excess cash flow after all expenses are paid.

Sometimes, the smaller fund sponsors are willing to be flexible with liquidity needs - as long as it doesn't impact fund operations and they have some excess cash on hand.

To manage the personal risk, I am thinking of purchasing an excess (umbrella) policy of $2M that covers me and my personal assets (If I had LLC, I didnot have to worry about this)2.

Companies that write Single Family Rental Dwellings have different appetites depending on things like:- proximity to the coast- fire protection (ie Hydrants & Paid fire depts. vs Pumpers and Volunteers)- what their results have been in the areaAll that can cause the company that is best for a town, area, age of building, etc to vary.

Also, the opportunity to buy a home there 6 months ago, at those prices, has disappeared.One last thought...if you buy a resale home that has been remodeled and includes the new code requirements for roof and windows, your insurance will not be excessively high.

The good 'wholesalers' I know are also flippers, often holding a Real Estate License, simply wholesaling the excess deals that they spend good time and money to find, analyze, and put under contract. 

Many markets have changed dramatically in the last year, with CAP rates dropping as new investors poor excess cash into REI. 

[Looks like my new mortgage payments would be similar as my current from using mortgage calc. with pmi.]My excess cash is $52,000.