I waited for this moment in time lol, I have the old chinky original blue DS, and then I bought the Palkia/Dialga Special Edition DS Lite now to continue the trend! You could probably sell your current one and buy the special edition one for not too much of a loss.
As for which game, I'm getting both... buuut my main game will be X. I love Xerneas and Froakie. Yveltal and Chespin will be part of my Y team.
And yes! I really enjoyed my time in Toronto. It's a small city, but there's so much to do and see. It also has a large gay community so finding things to do at night was fairly easy. Montreal as well, it was gorgeous the last time I went and I really want to go back again. Where in New York have you been?