I would get a LL/tenant attorney since no one really knows how the courts will react and an atty will have the best chance of knowing how the winds are blowing. 

Because honestly, at one point, I considered his offer and was afraid of the possibility that if I didn't accept I'd be taken to court and be responsible for putting my children on the street, and I can see those types of scare tactics and resulting emotions being enough to scare someone into complying with a transaction no matter how laden it is with misrepresentation, non disclosure and fraud it could be.Again, I don't know if I misunderstood the laws and regulations or not, I could be wrong.

At the same time, talk to multiple lawyers in your area--your area--that specialize in evictions and are in that court room ---your specific areas court room--all the time. 

There is a lengthy discussion comparing and contrasting the "broker" and "finder" parties and their role in the transaction in the court case described here: http://law.justia.com/cases/new-york/other-courts/2010/2010-20104.htmlWhile I realize this does not apply directly to the topic at hand (Wisconsin), I and other BP members in other states should find it very informative and educational.

Move out time came and they hadn't even started looking for a place etc etc. 2 weeks out from the court date for the eviction they upped and moved and didn't even request the funds (not that I would have given it to them anyways because they were 2 months past the agreed upon move out date).

Would a court allow you to collect twice- make a windfall profit on this mistake in renter judgment?

Also, since you never gave the keys for possession, highly unlikely a judge will even allow you to deduct per diem rent from the SD.After losing a couple of court cases on scenarios similar to yours, we huddled with our attorneys, who recommended charging a Holding Fee.We have a Holding Fee Agreement we require prospects to sign to hold a property until they later sign a lease.

In San Joaquin County (CA) it's taking up to 2 months for the court to process an initial filing of the UD action (they do notify the tenant of the action). 

@Will Gaston  What they try to get here is 3 per unit but there are a lot of 5 bedrooms so the ordinances have been taken to court several times. 

So even if you pick a state with stronger protections like WY or NV, the cause of action arose in the state where the tenant fell, so likely that the court where the accident happened would have jurisdiction.