Owning a few typical properties in Cleveland gets you an extra $500 a month.

With the extra cash flow, you could strive to acquire additional income-producing properties over time.

Setting up direct bookings is a great way to save on fees, but you’re right—it requires extra effort to ensure everything runs smoothly.For vetting guests, start by asking a few questions when they inquire, like the purpose of their stay, how many people will be there, and if they’ve stayed in short-term rentals before.

Half of the PM's down here can't read contracts, don't know how to inspect a property for damage, etc. - they just use whatever contractor is giving them the most free stuff at the time.  

That would be a helpful addition to your plan as you would further reduce your cost of living.Also don’t forget from that $600 you are planning on getting in cash flow you have taxes, insurance, maintenance, capex, and vacancy to consider.With two homes, you may want to keep that extra $20k as an emergency fund rather than spending it on a third property and then be left with no emergency funds.

I might also subdivide the other property and sell half of it. 

It taking half a day or a full day for someone to show up is completely commonplace at a hotel. 

It's easy to obtain, costs very little, and doesn't require extra, on-going effort to maintain.

This would obviously reduce my cash flow on both properties, as I would be paying the minimum HELOC payment plus extra towards the principal to pay it off quickly.

Over half of the things you said were literally false accusations based on your emotion on the situation and I’m not entertaining that of course.