I am just starting my first house hack and want to set up the tenant with auto-pay.

FYI - They will no be able to handle your primary home or auto, just the rental properties.

Second line of defense is your auto insurance. 

Auto insurance- business expense, gas for the car - business expense.  

Have you noticed the type and age of the autos in the Walmart parking lot?

Cable TV, streaming services, leased autos, financed autos (sell them and buy something you can actually pay cash for), and any subscription (personal or business) that doesn't increase your financial position.

Another issue, auto policies should have a business exposure, if you are conducting business and have an accident you may not be covered.Errors and Omissions coverage is a separate policy and usually covers errors, omission, implied warranties and negligence on a deal by deal basis, it's cheap if you can get it.No insurance covers intentional illegal acts, so if you choose to do a shady deal that violates law, it could be on you.An LLC offers some liability protection for those who can operate with an astute business knowledge, but there are so many ways to foul it up I'd say be insured!

You can set your credit cards to auto-pay each month so you can't forget - but you still need to budget appropriately.

That could be credit cards, auto loans, etc.

If you get an umbrella policy, it may be possible to list both the LLC and your personal names so it covers over both your new home, your autos, and the LLC property.