Once I get to a point that it is making enough per month that I feel comfortable taking money out of the business that would be when I get to the point that it is worth have a specialist assist me in all deductions, credits, and future items that will help me to transfer from a W2 to working for myself fully.

The biggest problem I see is that most of those items should have been itemized from the tenant deposit.

Most markets are competitive and a mere $10 a night could cause someone to book another property over yours which could cause vacancy and loss.

Furnaces are one of the most expensive items to replace in a property.

Improper reporting of big items such as mortgage interest. 

I know it's a long shot, but I'm currently having lawyers review the signed subscription documents to see if there's any way to minimize the losses here. 

I had clients in PHX  and Vegas that lost their 4 plex's because they went 100% vacant and stayed that way.. they owned 4 or 5 of them.. it only took about 3 months of negative cash flow and they were done.Max leverage loss tenants  lose property.. that's the formula..  

It's no different than those who hold stocks, then need to liquidate to purchase items.

@Gregory Wilson can you be more clear about what you mean about a loss?

I think you're confusing the quantity of items with curb appeal.