Well, this collaboration looked promising for a while, but ended up being a failure. Long story short, the programmer vastly underestimated the scope of the project not taking the sufficient time to set up and learn my existing system properly before he started the project of re-writing what I already have. Further, it's quite possible he overestimated his own skills and time available to work on the project in addition to having a full time job and family obligations. I expressed concerns about this early on, but he assured me it would not be a problem. Turns out I was right.
At 9 months past the agreed upon deadline I suggested that we ended the collaboration and he agreed, although he did say he would honor his obligation and complete it if I wanted it. I'd estimate we were at around 70 % of completion when ending it, but seeing how slow progress was and how unmotivated he seemed at this point, I just didn't have any interest in extending it. I don't want a collaboration with someone that's not willing to put in the same type of effort and sacrifices I'm willing to do.
I thought it would be the perfect match as he seemed skilled enough with a strong interest in finance and learning to trade. And I do think he was very motivated and inspired early on, but seemed to lose that along the way.
I think this is a common pattern for most people in life regardless of their pursuit. It's easy to be passionate and inspired early on dreaming about success, but most people seem to be idle dreamers who give up along the way. Some sooner than others.
If I ever decide to move forward with improving this application/system, I think I will have to pay it out of my own pocket just like I did with the original application that I already have in my hands.