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

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.  

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. 

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

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

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.

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

  $50/sqft for a full interior and functional update, $100/sqft for a full gut down to studs, $150/sqft for newcon .If these numbers make sense I would want to visit the property for a true estimate, where it would be line item work scope development. 

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