Contractors won’t even answer the phone, and even the RE folks I’ve talked to have troubles.

Thats not to say some might be desperate for business, but thats where it becomes your job to interview them (over the phone should be fine).

Any recommendations on a user-friendly PM software that has mobile features and owner and resident portals?

He now says he wants to "train" me to manage his properties, as if it would take a genius to pick up a phone and start building some relationships with decent contractors. 

By this I mean credit check, current employer and length of employment if possible (last 4 pay stubs usually works adequately for me), previous landlords (don't use reference phone numbers check them yourself by looking up the address and getting the person's contact information from publicly available sources - if they're renting they may have something listed currently or in the past.

I will trade $100/month for rent on time/every time, care of my property, long term occupancy and no phone calls all day long. 

Their data for Expireds and FSBO phone numbers is the best out of any other company who offers a similar product.

Be sure to talk on the phone with any potential Realtor, PM or contractor you will utilize in Cleveland.

That said, if you are able to mobilize people to NOT invest in Indy, I won't object.

You might want to try calling these local municipal offices beforehand And talk to a helpful civil servant by phone in advance to make the most of your visit and minimize the amount of time you spend in person during this pandemic bc govt offices are incredibly backed up and stretched super thin right now.