So while we have a  quicker eviction process to hopefully limit a landlords losses collecting for damages is difficult at best 

We will pay no more for loss of, or damage to that property than the proportion that the Limit of Insurance under this Coverage Part for the property bears to the Agreed Value shown for it in the Declarations.b.

My question is hypothetical, though at one point I was considering buying without much $$ down on the assumption that any penalties I took in financing would be offset by losses on not being able to jump in at the bottom of the market.

The least regulated area of lending is in true commercial areas, otherwise you're likely in violation of something.Really, they are considering regulating pet food production, seems like there are few aspects of life that are not regulated and there are still people out there who refuse to accept some things or who have decided those rules don't apply to me.Not picking on anyone here, just saying that it seems to be the case in general.

Sometimes you just have to cut your losses and move on.

They always take off just as @Matt Buckels said.I have one raccoon that comes to my front door and eats cat food a couple times a week.

Food for thought.

Unless you have enough passive income to offset, passive losses do you no good.

The good thing is you are located in Illinois,I am guessing you dont have to pay a Franchise tax which is not dependent on Income, but a priveledge for been allowed to do businessin the State....California is an example even if you have Loss, an LLC MUST PAY $800 to the Franchise Tax board every year,for that priviledge, however the income correctly will be pass through via a K-1 to your 1040 return

Are you insured for every loss or just these??