So the first stages of looking up ownership/investors and writing letters to both parties seems easy enough, but I'm curious what this contract deal seems to look like.

You'll either want to create a partnership agreement or form an LLC and create an operating agreement, which will incapsulate both of your rules, responsibilities, rights and terms of the agreement.

These are not particularly onerous, and, quite frankly, are probably a good rule of thumb to follow.  

The billboard company has 6 years left on their lease and as with any major billboard company they have an easy out in the lease(90 days).

PROACTIVELY Structure the deal.HOLD the property, refi and take out cash repeatedly if you need it and current lending rules allow ( that option cycles about every 5 years!)

I suggest these area because of the tenants usually be great quality, section 8 (government housing authority) qualifications are easy to clear.

It really is easy that way.  

Xero has come out with a self employed version (think it is free or low cost)  that makes it super easy to swipe one way for personal and one way for business.  

It is that easy to gain more knowledge and be more skilled when it comes to the real estate industry.

Proforma upside are not usually easy to get as most tenants have been in place for a LONG time and can't afford the current market rate.