I was going full speed ahead to sell it, but then I thought why not continue renting it out, and get a line of credit and invest the proceeds into cash flow positive investments?

I guess that would mean, if my calculations are correct (go ahead and check them), if you sent "mailing" to all 100 and only got two responses that is only 2% of returns.

Keep pushing.  

You certainly have no reason to think that you are "all that" and he is not.Playing gopher to a successful guy can be a good way to get ahead, but it is not inherently impressive.  

If after 12 months I don't see any significant progress then I will go ahead and devote my energy to getting my MBA.I'm honestly just not sure on how to start this 12 month project.

Yes I plan to make this my career so planning ahead is key.

But, if you're the seller,you will want to push for a larger down payment at P & S.Also, depending on where you are in MA, you can check to see if Redfin works for you're area.

Keep pushing forward to Success. 

Much of both Dodd-Frank and the Safe Act was written at a 50,000 ft level, with interpretation and implementation pushed off on states.My advice, if you're serious about pursuing owner financing, is to find a good RMLO to handle your buyer intake & qualification and the servicing of your loans.  

I wouldn't have asked for input/advice if I were to blindly push through this deal, esp. considering it would be my 1st.