I think he's really into me, but struggling, do I help, or does that hurt his ego?

Yes of course .... you know all his stresses , problems and issues and you also know how much extra nice , caring , pionate and understanding he has been towards you -- SO , if you plan to keep him and if you plan to keep your relationship with him and go on further also .. you must help him , if not financially , at least morally , encourage him , inject confidence in him , be with him , share and discuss his problems , get involved , And ure him that he is not alone in his struggle .. you are with him.... such boys are hard commodities to find these days and I think you are lucky to have him loving you so much .. reciprocate if you love him too and be his soul mate