I know you have a lot of things to think about and some tough decisions to face. I wish you luck on that! Whatever you decide to do, make sure you are true and honest with yourself. Sounds like Theatre is your passion. Then pursue theatre. Like others suggested, get more experience, maybe go to a bigger city, but not NYC. Look at Chicago, Boston, Atlanta, Cleveland, San Fran, Dallas, Phili, Memphis etc. You can find a lot of great things in those areas that will help you prepare for a potential move to NYC. Sounds like NYC is in your heart too, but maybe you can persue that dream a couple years down the road.
Just don't compromise your dreams. I know that from experience. Theatre has always been my passion, but as I was finishing up college, I thought to myself "what now?" I wasn't told I could have a career in theatre, not being an actor. So, here I am, years after college and nothing in theatre for so long, working my way back in.
You can always do the Grad School thing and do the Theatre stuff on the side. That way, you know both sides of your career choices, as well as more experience. then go from there.
Sorry, if I wasn't very helpful (probably not!). Let us know what you decide!