Hey David, just depends on your appetite and schedule.

I would think pursuing the issue with a lawyer will end up with legal fees in excess of any settlement. 

What is your appetite for rehab?

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.