Then a couple years later, discovered that a piece of paper was signed at closing which was never read and in fine print says something about the home being owner occupied throughout the duration of the mortgage... wtf?   

Sold 1yr later Lessons learned?

Forcing the seller to sell because they initially agreed can be a recipe for disaster later.

Apartments for me, is not user friendly at all, it almost crashes every time I touch the unit photos, and it will approve my listing then deny and unpost it a week later.

As long as they were being held and use for investment when you sell  othem.If you 1031 from A to B and then later convert B to your primary residence.   

Well, election 3-4 weeks later definitely ran up  equities.

Initially, tell him the considerations with the options and later ask him what he thinks of the options, then explain the considerations.

You should not have allowed access and now you are going to live the old adage of "it's easier to give slack later than to real it in." 

Unless otherwise stated in this Agreement, Tenant shall establish their own utility accounts, effective no later than the lease start date, pay all utility charges, and maintain accounts in good standing.

He was a real estate speculator and later a wholesaler after he went BK.