Do you cover items such as lawn maintenance, extermination, alarm and cable services?

But I would be missing items necessary for taxes, etc.

Hold Harmless & Indemnification clausesAs well as other items.

Highly agree with Nathan - Buildium is a Nightmare to use for STR, it is not appropriate at all and prone to a lot of errors due to the sheer number of manual items that need to be adjusted in there. 

COSTS:  I would look at any-and-all things needed to run an STR including items that are often done by owners--for example, property management.  

If you set out to do the items I shared regularly you will actually cut down on liability and if a liability event occurs you will be far better prepared.

We asked them to address 5 items that we saw as the most expensive and/or critical.

Great thanks @Michael Smythe, in your experience can you itemize the tenants that have the Resident Benefit Package? 

There are lots of due diligence items to complete to make sure permissions and titles are in order.  

Unfortunately as good as TurboTax and other online softwares are, they don't always pick up the most beneficial items with rentals.