For me, these things would be major, major red flags. There are many couples out there where the wife makes more than the husband. For him to feel emasculated by not being the primary breadwinner would mean that he has values and priorities that are not compatible with mine. You may not feel the same way I do, but if you do, this is a discussion you need to have with him sooner rather than later.
I also agree with this.
Be very sure you can make the apartment rent by yourself. Not only is that protection for your own credit rating, you really do need to know you can depend on yourself. The ramifications are lifelong; sooooo many women are unable to make hard decisions in their own favor because they are financially dependent on a man.
You need to learn who you are before you pledge everything to a partner. The best relationships are made from equals who acknowledge the needs and strengths of their partner,
in my experience. It might be best for you to scale down your dreams for your first "real" apartment to one you can afford by yourself.
If he does end up helping with the rent and having his own space in the apartment, that would be better for your relationship in the long run. You have the help financially; you've addressed his request for equality in your relationship; and you have the knowledge of knowing if he walked out, you wouldn't take a hit financially as well as emotionally.
You two aren't married, and currently aren't on the path to get married (not planning on getting engaged until you are financially "secure"<--good luck!),
so don't treat this as a marriage. The expectations are that you'll have a roommate, not a life mate. You two just happen to like each other a great deal and have been dating for a long while. You both seem like you're not ready to be life partners, so relax and give yourself time.
About going on Spring Break... I see that as a symptom of you two not being ready to settle down. He won't talk frankly of his real finances, and you aren't ready to compromise a good time to make him happy.
Think about that. How serious are you, really, about this guy? That should help you make this decision.
There's nothing wrong with being young and acting young; just realize where you are mentally, and don't make promises you aren't ready to live with. Always give yourself a backup plan!
Hope that helps!
Brandie