I am really considering making a call at this point because I just don't like the principle.

You will have more flexibility with this product to include setting up Classes and Location which is not available in the Simple Start and Essentials online products.You will want classes for grouping transactions, and locations for identifying individual properties.Hope this helps...

Start with 2-4 units before commercial - same underwriting principles but way less complex.

I know certain parts can be more cyclical than others, but some could be cleaning up shop & optimizing more to reduce their risk & protect their capital.I have followed most of the same principles they have taught me on my own. 

Also, on a fully amortized 30 year loan, the principle pay-down is negligible in those early years of the loan. 

Yes, interest rates (although the payments are interest only) and points are higher than for a bank, but the advantage is that good hard money lenders with whom you have a relationship will lend on properties that banks won't touch, have minimal underwriting, allow you to make what is essentially a cash offer to the seller, close quickly, and give you their input for your project along the way if you need it.

One should backwards plan as much as possible, synchronize work to quickly get the work done on time to reduce holding costs, then always ensure you follow good principles on making a good deal.

As we are entering tax season I am wondering what Expenses I can write off and if I need A 1099 for my Co manager who contracts out the cleaning team that I am essentially paying for?

If you don't pay down the principle later on when you REALLY want/need more cash-flow you still have the same principle to pay on.

When you write a lease "for a judge," you are essentially protecting yourself against the legal principle of contra proferentem.