@Elias Hubbard ok, I think the issue is that your Home and Auto insurance carrier can not handle a mixed use building. 

If you’re concerned about guests leaving windows open those same thermostat apps/software I mentioned above can auto-set temperature in response to windows or doors being left open.

Another reason I'm glad I have smart thermostats is that I've had 2 guests this summer change the fan from Auto to On, wanting constant airflow I assume, despite ceiling fans in every room. 

We use Streamline and can send auto emails. 

My List:- Auto Generated Smart Lock Codes (built-in integration through channel manager) - Set Smart Thermostat to Home Setting 1 Hour Before Guest Check-In (custom automation I created using home automation hub, channel manager, and digital automation platform)- Set Smart Thermostat to Away Setting @ Check-Out Time (another custom automation)- Whenever someone books/cancels, that information is automatically ingested into my database. 

For the personal umbrella, use whoever you have for your current home and auto.

I also offered my tenants a small incentive (rent discount) to set up auto-pay.

I have seen PM companies before make an error in setting up listings and inquires have gone to an inactive mail box or there was no way to schedule auto showings.May be worth contacting the company through one of the ads to make sure everything is running correctly.

In fact, in my case, it’s guaranteed that rents go up, it’s in the lease that there are yearly increases and that the lease auto renews unless either party opts out.

Same as an auto mechanic should not care how much taxes a real estate investor pays when negotiating the cost of an auto repair.