I just started riding an alpine board 2 seasons ago. Im from st.catharines and ride at kissing bridge. Since we live and ride at pretty much the same location, and I just went through the same process, this is what I would do, if I could do it all over again.
My suggestion would be to get boots first. Since your so close, go visit Andrea at yyz, and try on the deeluxe boots and watch for heel lift, to get properly fitted for boots. If they dont work, get some upzboots.
Get binding after boots, as the sole length is drastically different between upz and deeluxe. Sole length dictates binding size. And I highly recommend stepin f2 bindings, the convenience of stepin is simply amazing.
Board, get on Bruce's build list for an early December build. As others have stated, best bang for your buck and he rides the same icy hills as us, so he will know exactly what to build for you. Once you have boots and bindings, go visit Bruce before your build and demo a couple boards to see which you like better. He will set up your bindings, give you a handful of boards, and if your lucky, meet up with you at mslm for a couple runs, and give you pointers on your riding.