So, that you may not be able to start the eviction process until the following month, but it was already mid month when you received it so, no significant loss of time there anyways.

House hacking right now in many areas will be at a loss, but less of a loss than owning something with no income coming in on it.

It can be challenging for 1-4 units depending on the property characteristics, your loss history/other rating factors, and location.

So similar to golden era of active RE having possibly passed due to higher interest rates, I fear it may also be true for syndications (I am in one syndication that I fear an equity loss which would be my first time if this comes to pass).  

He's not an accredited investor so he can't deduct losses on personal income. 

I need to know if I will be able to expense this and have a loss for this year or if I will have to expense it over 27.5 years, $234/yr.

As an EMD lender myself often there are late fees baked in to the agreement which mitigates the loss of return if the deal runs long. 

.), on paper my properties are functioning at a loss (great for taxes, terrible for DTI). 

Besides I bet this guarantee is for a limited time (it's often for one year only), whereby the profit the developer makes on the sale of the properties is much bigger than the potential loss he would incur should the occupancy fall short of the promised percentage.

I'd like to charge a per use fee to at least help recover the cost of repairs each year or buy new machines.