I personally would be careful trading options with borrowed money… seems like a risky proposition.  

I personally like to use attraction or content marketing; better use of my time, less rejection (which takes a psychological toll on you) and higher quality leads.

But he has a fulltime office person ($??

Start low if possible, offering yourself to the companies, and listen a lot of podcast from people that did this.- Partner is always better, but to put your name out there you have to do it yourself.

If your friend is a super responsible person I’d be troubled by this.

I contacted the power company, and they directed me to the tax assessor's office to inquire about obtaining a separate address for the pool house.

The first step toward this goal is for the city council to recognize the harm caused by maintaining a high commercial tax rate, which drives companies away from the city.Hopefully, we can explore more avenues to generate employment opportunities for Worcester residents, empowering them to work and sustain themselves.

For background this is my first investment and I own the property personally not with an LLC or anything of that nature. 

I would think not... but you could possibly set the master as a PMC so that it doesn't actually "own" the other companies but manages the properties for the LLC's. 

I personally would put down 20 percent and keep the rest of my cash, even if it meant I wasn't "making money" in the beginning.