He dressed like a homeless guy in an ancient truck to collect rent (ok, his normal working on rentals outfit or working in the yard duds, even now).

If so, you win, with attorneys fees paid and possibly punitive damages. 

Any entrance upon or movement across the Roadway be any person whose rights arise under this Easement shall be conducted thereon such that it does not damage the Roadway or any improvements thereon, or unreasonably interfere with the rights of free use and enjoyment of the Roadway or any improvement located thereon by other persons whose rights arise under this Easement, or otherwise unreasonably increase the burden on the Roadway.Any person damaging the Roadway shall repair and/or replace any damages they may cause to the Roadway or any improvement thereon such that it meets the reasonable approval of the Parties.

The big "McDonald's hot coffee" awards you hear about are extremely rare and contain extra punitive damages above and beyond the regular award due to long-term, sustained negligence from the losing party.One other thought to help put your mind at ease: I personally know over 100 real estate investors, and none of them have been sued for more than $5,000. 

Of course some permanent damage is done to the economy.

Covid-19 will likely hurt universities some and a bit of that damage could be long term.

I dress pretty casual in Chicago with buyers and business casual when sell side showing.

That you will pursue a financial judgement against him in court for all the unpaid rent, utilities, damages, plus your legal costs.Since he's young, I would recommend you actually pursue a judgement against him as this will follow him around until he eventually pays it.

I think this may slow or stop soon, but the damage in some places like Minneapolis is city changing.

DOM (Days on Market)No comps, or comps are too variedActive vs. pending ratioHigh tax assessment to value ratioInsurance:Property in flood plain or zone and on flood map requiring insuranceCLUE report, uninsurable or difficult to insureInsurance escrow or notLapse, adequacy of coverageProperty:SquattersFunctional ObsolescenceSeptic, onsite systemsWellLead or galvanized plumbingTerracotta sewerProperty preservationStructural damage (expansion cracks, main beams)Landscaping issues: retaining walls, bamboo, soil shifting, etc.No permitsIllegal BR size < 70 sq.