Can anyone recommend some good books that discuss organizational leadership and how to properly run/establish business operations. 

In my opinion, yes, it can be done, but you're looking into a bigger mess as far as the government is concerned.Lets preface this with I don't know exactly how this works either, but after a certain amount of people are involved you have to report as a Real Estate Investment Trust (REIT) and have to file extra forms related to your business and also after a certain threshold you also need to report members and their distributions to the Securities Exchange Commission (SEC) so they know as well.Being young (as am I) you are going to run into a lot of dead ends trying to apply for a residential loan with a business name.  

I know there are tons of productivity apps out there, but I'm curious which one(s) you find most useful for running a two-person real estate investing team.Thanks in advance!

@vladimir valladares,Or you can  just tack on the typical Agent commission to the sales price and run it through the brokerage office.No problem there. consider it what it is, an off market transaction.

Or what obstacles will I run into?

That being said, you may run the risk of being over-leveraged by getting into another similar deal. 

There is a group that meets in Upper Marlboro run by Sherman Ragland.

However, all the numbers I run do not present with a positive cash flow.

The more you get familiar with running the number, the more comfortable you will become and the easier it will be for you to identify a GREAT deal when it comes around.  

Essentially you need to run some numbers to see how much equity will be in the property after purchase, what your cash flow from the property will support, etc.I'd do a search of the BP site on "Creative Financing" and see what others have done.