Keep in mind that a low maintenance and repairs number can be a sign of deferred maintenance that you're going to have to pay for when you're the new owner!

So I can have something ready for them to sign if they want to finance my purchase.

He's been "signing for one more year" for 4 or 5 years in hopes to purchase a home of his own. 

This will determine not only how passive or active you want to be, but it will also will help you to determine what type of strategy you should implement to achieve your goal.

I know there are a few videos on youtube worth watching about how to generate your own leads and with minimal amount of money you can use options such as direct mail, signs, a website where distressed owners can input their information and it will relay them to your email. but definitely worth looking into. 

Broker's often offer sign-on bonuses like free or discounted business cards.

Also, I don't know your area, but I would use several valuation methods to determine market rent, and not just rentometer.

If I am only assigning the Option why do I need a Lease signed between myself and the Seller ?

To qualify, you are going to need a sponsor/loan guarantor who meets these requirements to sign on the loan.Your best bet is secure a 20% to 25% down commercial loan, raise money to fund the down payment, and find someone to sign on the loan.

I brought a cashier's check (I think for 5K) for the down payment and signed all documents right there.