I am not keen on returning any of this money back to the main tenant as it is very evident that the damage he has caused on the property with a rotating cast of characters and a pet is likely significantly higher than $2000.5) Legal fees and other costs: Can we include a demand for unpaid rent, legal fees, and other costs in the eviction process for our tenant or does this have to be a different suit?

He rotated between them, managing the managers.

It's a higher turnover market because college kids rotate throughout the years, but at an average of $1,000 - $1,500 PER ROOM in my market, there are some amazing investments both on and off market. 

If they don't renew, I'm forced to start a no-fault eviction, which strains the landlord-tenant relationship.

It might put a strain on the relationship, there are other things to line out though, that is just one item.

You can expect complaints from the neighbors once they realize teenage kids are rotating through.

Rotate out of BDCs to Govt debt as tightening lingers, and rotate from govt debt to equities as fiscal policy loosens.

Will it strain your marriage/relationship/family life to a breaking point?  

Some wholesalers have been known to engage in less-than-transparent marketing strategies to secure a deal, further straining the relationship.Questionable PracticesSome wholesalers may engage in practices that realtors deem unethical, like purposefully seeking out financially distressed homeowners and pressuring them to sell at prices well below market value.

@V.G JasonI think you're saying that for people who bought maybe at the tip top of what they could afford, if they take on more debt and/or variable rate debt adjusts and/or they lose a job and/or they get divorced, they'll be under a lot of financial strain / potentially unable to afford their mortgage.