If you add every financial account to QuickBooks that you use for the rentals and then use the Reconciliation feature each month to match the bank/credit card statements there's no way for you to miss any transactions.  

There are unique tax laws when you are house-hacking so make sure you work with a professional who understands them.House hacking makes your tax situation more complex.You purchased a property that is treated as both an investment property and a personal residence.

Any unique challenges anyone has run into?

They just don't offer online transaction downloads directly from your bank, which I never wanted in the first place, so I don't care that they stopped that feature from working on older versions.  

This is a unique strategy.

It is a specialty policy that covers the unique risks  of a vacation rental.In the Smokies, the gold standard is Southpoint Risk in Knoxville.  

Being that it's not really known as a tourist destination (but features some of the highest elevations east of the Mississippi River), prices are still very affordable offering very good ROI. 

Costs 9%.iGMShttps://www.igms.com/features/airbnb-team-management/iGMS provides multi-listing service management, automatic cleaning notification, automatic messaging, direct booking and payment processing.

My son will simply join the area/neighborhood group and then use the search feature for "housekeeper" or "cleaner". 

It presents a very unique opportunity to detach it from the city limits to remove undue restrictions that have affected the value and use.