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. 

I typically look on the MLS, but I would like to hear about some more creative ways to find a property.If it's on MLS, CreXi or Loopnet for >2 weeks without an offer - Odds are its not that great a deal.I don't know about creative, but you've got to build relationships with sellers/buyers.Best tool - It's called a phone.

I still want them to take money out and hold in escrow for the taxes.I had one lender after I communicated to them that I was going to be paying my insurance in full for the year up front and that I no longer wanted them to hold money in escrow for insurance, close the whole escrow account including the money held for taxes, and they sent me back all the money that was escrow, in which I had to send right back saying I still wanted them to hold money for taxes.It took a few phone calls to get that through to them.

People don't like to answer their phone anymore.