And if possible, would such need to be indicated in the current sales and purchase contracts?

At the most basic level, we would all like to think we know of the "indicators", but it would be nice to get your perspective. 

Some other research that I did indicated that if there are multiple owners which have all occupied the house for some 2 of the last 5 years, then they all can benefit from the 500k deduction (if they are couples, 250k for individuals).

Misdemeanor indicates it was lower in severity, but is was physical.

I have a guy (with 4 yr son) whose background checks indicates 700+ credit score, stable federal job (3X salary vs rent) for last 8 years, good references from past 2 landlords BUT had chapter 7 bankruptcy that was discharged in 2013. 

There were water spots above the kitchen cabinets, as well as some standing water in the basement, while disclosures indicated there had been no water issues on the property.

I was going to recommend mailchimp.com as well but it seemed to indicate it was not allowed as part of the spamming rules.

You indicate that you have some ideas, but would be open to anything that has a good ROI.

Haul away dumpster can indicate a renovation.  

Basically, anything I could think of to make it worth less or to make sure anyone in the room understands the negatives about the property I would not come out with guns a blazing once the bidding starts as in my opinion that would indicate to some bidders they are missing out on a deal.