2020Dad - I like you're response (mostly). Perhaps the only thing we are not eye-to-eye on is chasing the $$ as much as chasing the good person thing. No, I'm not judging you at all, I just realized over time that while the more money we had, the more things we could do....but I'm not sure I'm any happier overall than when I had little of it. (BTW, I started out with nothing myself - my parents weren't poor (nor rich) and we didn't ask for nor get any 'startup cash' - but we had about $50 in our bank account when we got married).
I guess if I had to make a choice, I'd rather my kids be good people than wealthy people.
"You don't want my money and all the headaches it brings, just stay where you are"
I guess I can sorta see where you see this in the article...but I didn't take it that way at all. However, given that you took it this way, I do understand your thoughts about it. 
What does all this have to do with baseball? No different in athletics. It is a big red button for me when the parents (who probably mean no harm) of college players talk about how hard it is to get there and we parents of young ones are dreaming.
Uh oh, I am definitely guilty of this - and you may have been referring to me(?) as one of them. Thats ok!! Because I certainly mean no harm. I guess I'm just saying that yeah, its hard, really hard! Way harder than I thought!!!! And once you're there, its even harder to stay there!!!!!!
And so I guess what most of us are meaning when we say this is something like, 'don't underestimate the difficulty, don't make it the ONLY goal, don't put your son in a position to feel like he failed you if he cannot get there and don't ever let yourself feel like you messed up in case your son didn't get there.'
Too many parents (don't think you're one of them) act as if a) its their child's God-given destiny to get there or b) if they just practice enough, buy enough lessons, attend enough showcases and be seen enough, it will happen.
Both or either a & b could be true...I certainly wouldn't know even if I had seen anyone's son, but I certainly have known a number of parents that believed a, b (or both) and were wrong. (I've known many who were right too!!).
2020Dad - I love the passion in your posts. I have a good feeling that if we lived in the same town we would have enjoyed coaching with or against each other. I am VERY competitive myself, as is my wife, and our kids have turned out to be so as well. I see it as a good thing. I think there are too many docile parents out there not teaching (or letting) their kids (learn) how to compete - they're doing everything for them. The funny thing is that I also think the Dean was kind of making the same point in her own way. At least thats how it struck me.