We cash flow about $150/mo on average, so any cashflow we have is completely wiped out by our depreciation so we're running it at a loss from a tax perspective. 

Depending on the wording of the contract that could put the EMD at risk of total loss. 

I know there is a concept of loss of rent insurance if there is a fire or something. 

Even if you hire all the subs and pay them as 1099's, in some states, whether or not some one is an employee under the workers comp laws are determined at the time of loss. 

Hi All,Please, I need your help understanding the new IRS law starting January 2023, which will only allow you to claim losses on your business for three out of five tax years.

Your time horizon is also important here, for a high end airbnb, I would plan on spending at least $20 a foot furnishing it, so you need to make sure you have the capacity to recover that cost too. 

These losses can be locked up if you're not a real estate professional (REPs).

Potentially if you meet all the requirement to deduct the losses against your W/2. 

I'm working with a CPA who is arguing that STR should be considered a passive designation and therefore losses in our holding LLC cannot be applied to my W2 wages (which are > $150k).

I'm surprised to hear this still goes on, but I guess people have short term memory loss.