As I read the advice about advocating for himself, I really feel obligated to respond. Definitely, in the course of any discussions you have, your son needs to develop strategies for dealing with this that work for him. Indeed, one of the things that many of the programs at colleges for first-gen students do is talk about how to have conversations about money-- from room decorating, going out to eat, etc. – that honor their financial realities. But remember that those programs also offer a community who are facing these issues as well.
So yes, there will be work for him to do. And yes, it is possible that your son may be able to develop and implement a successful, empowering strategy to deal with the bullying. However, it’s really important to understand that someone who is being bullied is already being belittled and in some ways “separated from the herd”. If you tell your son he can resolve this on his own and he in fact cannot despite his efforts, he will be further ashamed and belittled. And he may not tell you about it because he’ll feel like he’s failed and that he’s let you down too. So unless you have a really good plan and you are sure that he’ll keep you in the loop, I would not advocate for asking him to go this alone without talking to someone at the school. Given that your son is at the point that he wants to leave school, it probably has gone too far,. If it were my child, I’d also like to be sure that this wasn’t interfering with academics.
I would, in my meeting with the school, state that you’d like him to handle this on his own as much as possible but that you need their advice and support. They probably understand the lay of the land better than either you or your son. I’ve been thinking about you a lot, and a couple of things surfaced for me. First, if as you note, other boys are piling on, it sounds like there may be one or two boys who are behind this and that others are joining them as a means of not being targeted themselves. In other words, there are a couple of real bullies involved and then a gaggle of cowards. If this is the case, the school really should be monitoring what the real bullies are up to. They can be completely toxic to a community.
The other thing that I’d ask the administration – in order to help your son develop a strategy – is what other activities the school offers that are costless. If he can’t afford to take an Uber into town and hang out at Starbucks (or whatever they do in town!), there should be other things he can do that are free. Many schools have worked really hard to have “diversity” (including SES diversity) yet have done quite poorly on the inclusion front. (I read something from a committee that was working on this issue at one of the highly selective colleges often mentioned on these boards that noted among other things, they had a culture that “normalized affluence”.) A school that wants to include students who have less to spend will have activities that are appealing and free. Perhaps the school van goes into town or to a park that has hiking trails or Frisbee golf, the gym is open for free play, there are movies in the student commons, there’s a karaoke night – anything that allows a group of students to choose an activity together that doesn’t’ require them to reach for their wallets (and with a little luck, is preferred to the activities requiring a wallet!). You should ask about what is available so that you can counsel him on how to respond when the kids are going into town. It’s fine for him to say “I don’t have money for a trip into town so am planning on staying on campus for the manhunt game” or whatever. It’s honest, it doesn’t make him seem forlorn, it leaves an opening for someone to pay for him, and it allows the others to join him. But if the school doesn’t have many of those opportunities, it really is segregating him and making it difficult. While you may not be successful in getting them to think about this, it will help you and your son understand what his options are and what may be realistic in term of expectations.
Please keep us posted and good luck.