Uh oh, Dylan really needs to come clean ! And Chuck needs to stop fretting about who has money now. If he becomes a Chef he'll eventually make more money than Dylan. Will he then leave or want Dylan to feel bad about earning less? Of course not, so why does he think it matters? But I guess Chad had already hinted at Chuck being a gold digger, which is pretty absurd, when he didn't know of the trust fund. However, those nasty remarks may be one of the reasons Dylan has been reluctant to say anything.
But why did he say in ch 2 he couldn't afford going to hospital? It worked at the time, but now it seems quite weird. If nothing else, his dad woud have paid.