Please don't take this the wrong way but only you can answer the question of when you are "ready." And if you keep waiting until the perfect time comes, where you can slip into a new community flawlessly, seamlessly, (almost magically?), that day will likely not arrive for a very long time.
Of course, you can plan for this (which you are, obviously) and get some great advice and insight from others to help you be prepared. But like a quote from The Matrix: "I'm trying to free your mind, Neo. But I can only show you the door. You're the one that has to walk through it."
I know this isn't easy, please don't think that is what I am saying either. I haven't returned to college since I started my transition several years ago, and I am "still" a little scared of returning to school.
What were you born as? I was born female but that's not what my birth certificate said when I was younger. Simply put, I was born transsexual instead of cissexual. My secondary sex characteristics didn't match the gender my brain told me I was. And there will always be someone to argue the "legitimacy" of my womanhood but I don't need to win their approval and don't need their validation to know who I really am, mind and body.
What would happen if you waited? If you want to start the Uni as a guy, then start it as a guy, that's a pretty good indication to me