Have a goal and steps to achieve it, with milestones and deadlines...I don't want to sound judgmental, but you seem to leave a boss for another boss.

Since it's family, it's arguably more important to ensure you're doing what you can to preserve those relationships.I would recommend having a contract, complete with milestone check in dates so there isn't an unending sense of feeling like you're on the clock. 

Also if you can make a connection with someone or even the agent, I would be willing and offer to pay someone to check in on the progress of the project during certain milestones.  

Josh,Congratulations on reaching a great milestone.

Rich:Thanks for sharing your experiences here, it really enriches the rest of us.Perhaps you might share what sort of 'milestones' you set for your grandkids for receiving their shares.And you mentioned excluding those with drug or alcohol-related convictions.

Why was the bank approving the draws even though the presumed milestones were not achieved?

This way you're paying the contractor in installments as the project meets certain milestones.  

Because of this, I negotiated a great rate from him, with specific bonuses in place if he hit certain milestones.

Today marks a milestone in the industry.

For a job that big just pay downpayment on first job and pay on milestones of completion not 99 percent complete but 100 complete.