If I know I have another agent across the transaction working with me on behalf of the buyer to successfully get buyer and seller to the closing table, it is more comforting than thinking I could be dealing with an amateur buyer or worse a dishonest buyer that doesn't know what needs to happen. 

Thus, you'd have to somehow find private money to fund your venture which would come at a ridiculous interest rate to compensate the lender for the risk you're bringing to the table with your inexperience and/or lack of collateral.

When you bring nothing to the table, it’s because you’re producing something else, which is just as valuable as money.

It's tough to know as sometimes these deals take massaging into place.

I’ve been friends with him for 5+ years and I trust him, I just worry that I’ll be the only one bringing knowledge to the table from researching and he’ll just learn on the job.

If you can't "refi" with a sufficiently large loan to pay off the first loan, you need to come to the table with more cash (I guess a "cash-in" refi). 

However, I didn't want to leave money on the table if tax deductions were available, so I looked into it and nothing really qualifies.I can't give them free rent and then deduct that, because money hasn't changed hands.I can't donate money which they then use to pay me rent, because that's just manipulation.I can only deduct true financial donations or if I give them the property, meaning they own it and are on the deed.

Even with options you need to be prepared to cover.As a real estate investor I only need to bring 20% to the table fir my purchases and get tax benefits I too.If your stocks consistent performance at least 4-5x better than my TK investments I suggest you keep doing them, especially if your TFP is much more than 10 years in the future.

They do go off the table faster than other so you will need to capitalize on the opportunities when you find them. 

@Nicholas Covington   it is labeled as mixed use in property report and currently has a massage therapy company and a clinical psychologist renting the building.