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.  

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

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

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. 

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

It's not a one-size-fits-all answer, but hopefully this gives you some food for thought.Whatever path you choose, I'm here rooting for your success.Jasper & PatTurning investment visions into REALITY in Phoenix, AZ - Ranked #1 for residential real estate growth and opportunity by PwC

@Andrew Frishman - here is some food for thought to get you started: https://www.biggerpockets.com/member-blogs/11782/84402-how-to-evaluate-a-sponsor Feel free to DM me with any specific questions, I have invested in multiple deals as a LP and as a GP.

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.