With my increased AirBnB performance, I decided to turn 2 other rental homes into short term rentals and decided it was worth investing in proper training to make sure I was doing it right. 

- Insurance Implications: How might allowing pets affect my homeowner's insurance, and what steps should I take to ensure proper coverage?

They often offer coaching programs that can guide you through the fix-and-flip process, including how to properly assess properties during walkthroughs.

Sounds like the county failed on multiple levels including not giving proper notice, not sending notices to the correct address, etc. 

You should have boiled them down to the following lack of proper due diligence.  1.  

They can limit what property owners can do, including house hacking.Even if the city has no restrictions, if legally binding and properly recorded, covenants can enforce rules that supersede local ordinances for those living within the neighborhood.

This likely means living in Louisville proper, depending on the job's location.

One city near me is checking all garage enclosures, giving nice notice to get them permitted, which they may or may not grant, and if you don't get it properly permitted by December 31, says they will start fining people. 

How are out of state or local investors reacting to the ordinance to register with the city?

@Gerald Koonce Private lending from family members is allowed with proper documentation and compliance.