I hired a contractor with a solid reputation for working with international investors, and we agreed on a total cost of $495K, to be paid in stages.

Relying on someone who has their 'own team' to run your rental business is a severe lack of internal controls in my opinion.

Good Cause Eviction, the 2019 TPA, the history of moratoriums, and the clean slate act sealing criminal records and other offenses. 

I dont know how many units you are talking about, my biggest problem was tenants having easy access to me.I finally decided to use a software and got an internal property manager so moved away from it.Currently setting up the maintenance request portion of it, so will see how it goes.

It will be money well spent.Also, criminals know how to check which properties in the area are STRs and might be vacant during most of the winter.  

Also, was there a background check on the tenants possibly having criminal backgrounds and or background check to determine if the tenants had ever been evicted in the past?

This is partially offset by high international immigration and births.

Both domestically and internationally.  

Viewed this way, it becomes a toss whether domestic or international investing is the riskiest.Let's give you the benefit of the doubt and assume that investing internationally is riskier.

.- Do you want to manage the new system internally or have an outside vendor manage it for you for a small fee.- Would you be requiring custom changes often to your digital workflow?