Auto reminders for lease renewals, quarterly/annual preventative maintenance programs.

However, when I shopped around, I found that State Auto gave me the best rates for homeowner's insurance.

Use rent collection software - most of them have ACH "pull"/auto withdrawal available.If the tenant wants to wire money that may cost you on your side.Don't allow tenant to control the conversation.Give two options:- here is the account info and bank - they can walk the cash or deposit to your bank and deposit it- ACH/auto withdrawal.That's it.

Seek to understand and negotiate a compromised solution.Suggest he set-up "auto pay" with his bank.

It turns out that the teenager is underage and thus the father's auto insurance is not going to cover it since the teenager wasn't on the policy.  

I do not auto book and I ask most the same things, but I don't ask how many as that is usually in their booking request.

When I was in real estate I would set them up on our Auto-Notification system through our MLS. 

_______________________________________________________________________At some point the insurance company will not allow you to add more units to your Home/Auto package and force you to put your additional properties/units onto a commercial policy. 

On Airbnb you can set parameters within their auto-pricing system to maximize rents.You said it yourself you don't even really need to screen don't even need to screen.

It would turn into a nightmare super fast even with auto payments.