I think that we DO forget that these mid 6 figure salaries aren't what they seem to those of us in the workforce.
If I make 50K this year, odds are pretty good that I will make a little more than that next year, and a little more than that again the year after, and so on, until I retire, many many years from now ( I'm 27)
If Bucholz makes 300K this year (Im just throwing that # out there), first he has to pay his agent, then probably 2 or three other people, then he has to travel with a bunch of guys making millions and try to keep up an appearance with them. (Yeah, not that big a deal, and can be managed correctly. I'm just saying it's easy to mow through that).
Most importantly though, his career has a limit. I can work at my craft and become more valuable as I age for 40 years if I want. Can he? What is the average lifespan for a minor league pitcher, even a top ranked one? How many years can he expect to get out of his "career"? 1? 5? 20? If its twenty, he has nothing to worry about. But the odds would say that lifespan is much much closer to 1.
What does he have when that career lifespan is over? What marketable skill does he possess? A high school education? Teaching kids how to pitch? This is one of very few job markets where your skill set is actually diminished over time
The truth is, me with my MBA, or even better me two years ago with my undergrad, may be set up better off for the duration of my life than a pitcher with a high school education who makes 400K for 3 or 4 years.
Now, I'm not saying I feel bad for the kid, or agree or disagree, I just think when we talk about the salaries of a minor leaguer who may never get another contract again, we shouldn't act like they are set for life.