The rentals pay for all the fun stuff.

You need to do this stuff because it's too easy for tenants or potential buyers to neglect the water bill, and the Detroit Water and Sewer is high.

He also had gray hair and a few decades under his belt.

I hate to pull the grey hair card but 20 years of collecting rent is 20 years, how many years have you been handling rental properties?

Can such a model be managed remotely, but hire someone per hour as needed for in person stuff?

Almost all our stuff is in montrose, museum, med center, etc.

This stuff happens with condos and townhomes sometimes, and very frustrating.

But infuriating that people are out there doing this type of stuff

Just know your stuff. 

Also, compared to the stuff I deal with in my day job (IT), it's not that bad, and ultimately, I'm in charge, so if a tenant or a contractor is not working out, I invite them to leave within the law in my state.