So I stick with my initial assessment - insufficient due diligence was done at outset. 

When did you change from your initial project management tool for 2-3 properties to something more sophisticated for managing 4-10 projects at once.Greatly appreciate everyone's thoughts and contributions!

One challenge about short term rentals is that they are not always booked and initially getting those bookings to a minute, people were more hesitant since we didn't have the super host and premier rating.

There are plenty of short term rehab loans available that will help with the initial purchase, give you rehab money, and don't have any type of prepayment penalties.

My view if/when 10yr yield rates come back down to sub 3.75, there'll be a lot less dry powder on the sidelines after the initial euphoric lift which may be influenced by seasonality but will not show any real course of duration.

I can tell from your initial post, that your former co-workers (...you've really got to love saying that!...)

And we rarely need to use them.Tenants sign and initial each page of the condition report at signing, we quickly go through the property and let them take as long as they want.Ideally at move out they would sign the condition report, but this is nor normally done. 

Expenses for initial repairs before renting are usually capitalized and depreciated.

Property owners are almost always named as a defendant, at least initially.

My initial guess would be look at 1 bed 1 bath rentals in the area but is that the best way to estimate?