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.

And, in an ethical fund, the investment sponsor has first loss capital and eats any defaults dollar for dollar. 

With increasing client demands and a vision to expand, it’s the perfect time to bring new agents onto the team.

Mason,From an insurance perspective I would add, getting 5 year (or more if possible) Loss Runs. 

Since you have the cost segregation study to provide proof of the value of the roof separate from the building, you can easily write off the $450,000 loss.

We’d rather take low double digits passive with lower risk over 25-35% active with the risk of principal loss.