This is a great question. The short answer is no, I haven't had my kids do the crappy jobs. I have had them working from their mid-teens, but not at the kinds of grinder jobs I had. Maybe I should have. All three of them have done retail, or lifeguarding, or fast food. I did have my son go work on my cousin's real, working cattle ranch for a few weeks to get the feel of it (it's not a romantic cowboy life), and he's better for the experience.
When my oldest was in HS, one of her classmates was required by her dad to go to 4-5 adults that she admired and ask "what were you doing at my age?" Without fail, all of them said they had at least a part-time job. A valuable lesson for a teenager.
Maybe I should have had my kids take the real grinder jobs. It probably would have been good for them. However, they've all turned out to be decent, responsible adults, so I don't think I messed them up too badly.