It might be worth talking to a lawyer but not sure if it's small claims or worth it.Also, you might already have all of these things but for future prevention:- smart thermostat (so you receive alerts when the inside temperature dips below whatever preset you have)- Minut (or similar device) would also alert you to the inside (and outside) temperatures; for example, I have 2 devices inside the house and outside on the hot tub deck.

Use a tiered approval process to give them control over larger expenditures while enabling quick resolution of smaller issues.2.Proactive Maintenance: Implement preventative maintenance programs to reduce costly emergency repairs and extend the lifespan of property systems.3.Monthly Reporting: Deliver detailed monthly financial statements that outline expenses, rental income, and ROI performance.By handling their funds with care and providing transparency,  trust is built with owners, ensuring they feel confident in the relationship.Making Tenants Feel HeardHappy tenants are the foundation of long-term occupancy and reduced turnover.

I understand this may prevent me from getting the absolute best terms on a HML, so I'll turn to professional before I settle on a lender, but I'd like to start the shopping process on my own.

Explain your situation and see if there are payment plans or hardship programs available.The BiggerPockets forums have threads on tax liens and foreclosure prevention: https://www.biggerpockets.com/forums/41/topics/766025-surplus-funds-unpaid-taxes-in-foreclosure-saleAn experienced real estate attorney can advise you on your legal rights and explore potential solutions.Have you spoken with your local tax authority yet?

What specifically did you expect them to do to prevent them?

Including one that prevents a unit from being rented for less than 6 days. 

If multiple people chose another house for the same reason or avoided yours for the same reason, maybe you can pivot a little to prevent that issue being a factor for future prospective renters. 

In our student houses we use a programmable thermostat, but our building monitoring system has its own sensors and can override the wall thermostat and will not allow the temperature to get below 10C (50F) ... we are presently testing a new software load that will also prevent them from cooling the house too far in the summer.

There are, of course, also things like politics and tax policies preventing the New York side from developing its tourism sector to be on par with Ontario... 

Trump has said many times in recent days he wants to prevent evictions, but his latest executive order does not ban evictions.