If there is a different set of rules once a tenant stays a month, and there isn't a way to have tenants sign a lease using STR listing platforms, then what protects medium term rental owners?

On my end, I set my payment schedules, how it will be delivered, level of work I expect, etc.

Our long term goals are financial freedom, including matching my current salary with rental income in the next 4 years. 

Is there a reason you are set on having a local CPA?

I have started screening after the realtor screens them and tell the rules, setting expectations upfront.

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. - Training is in-depth and correctly sets expectations.

Now we are in pruning stage - trimming off the ones that are further away or cause us the most headaches, and adding those that meet our long term goals better.A very wise person told us early on that if we wanted 50 properties, we should plan to buy 100, and sell half to pay off the remaining assets. 

I've always had good success with midterm rentals on Airbnb - You just have to make your settings to attract a midterm renter.

I don't rent to anyone living in my own home, but I have known people that do who set up cameras in their own off-limits spaces, deadbolts for doors, etc.