@James Edwards You'll need to enforce your rules and regulations.

The bigger concern most STR owners face has less to do with liability for actions of guests using free WiFi at a rental property, but how having their "smart" locks and IoT devices are on the same network as their devices, forcing communications through older, insecure protocols, and exposing their furnished rentals to significant risk of compromise from someone with a fairly basic idea knowledge of Internet security and few web searches.

Make sure to be aware of the different laws and regulations regarding section 8.

I am thinking that is the spirit of the regulation - They don't want you using your 401k to put cash in your pocket. 

The free version that comes on most devices does not have that capability.However, there are free file conversion apps and programs online. 

The way around it is to use a PPM and set something up under Regulation D of the IRS code, but it's super expensive and you need a quailified attorney to set it up.

Become familiar with what the 6 ADU/JADU regulations allow and their limitations. 

The reason this is important is that it implies that duplexes purchased will be under rent control regulations (assuming a unit is occupied) regardless of if the new owner decides to move in (house hack) after purchasing the property. 

Recently there have been municipalities that have set guidelines (regulations) that prohibit denying a tenant for previous criminal convictions at least x-years ago. 

Regulations.