I can try to give you the mathematical version of why this is a terrible bet, but I will save the time and explain this way:
This bet has a better chance of winning than 50/50, that is true. But what you are risking as opposed to what you will get in return is not anywhere near what you should get. $385 or $440 should be more like $600 or $650, at least. And that assumes that the Cubs and Pirates stay like they have been so far this season.
I wish you luck, I really do, and this may work a few times, but overall, this system gets you closer to the outhouse than the penthouse.
HW