I can't say how many crews are run like his was, but I also don't think it's fair to assume that all those guys are making next to nothing. The roofing season is so short and the money good enough that I'd bet that having someone you trust to move fast while maintaining quality would be worth a significant amount over minimum wage. Having worked with him on my summer breaks in high school, it took me a full season to get to the point where I was even close to keeping up with his regulars. I'd also bet the money being pretty good, not bad, is why you see groups of the same ethnicity working together since they probably recruit and train each other whenever there's a vacancy.
I'm not sure if I understood correctly, that your dad's crew was mostly immigrants, why do you think it was like that? If pay was good and semi-skilled (easy to train), why mostly immigrants?
There are millions of immigrants in the U.S. who are legal; why would you think these people are not? I guess my point is, it's not a good assumption and has bad consequences: People having their legality questioned based on no evidence.
On one hand, I understand that people don't want to be challenged or to write dissertations for casual conversation. On the other, we know that misinformation spreading through 'internet forums' in the form of 'guesses' is a problem, that HN isn't a typical internet forum, and that 'guesses' are often challenged here.