Ok so if I may summarize your words. To the question "What gear would you buy if you had a budget of approximately $200 CAD or less?" the answers we got for the moment would be:
Headphones: Shure S215, Shure S315, Sennheiser PX100-II, Sennheiser Momentum (I'm personally not sure about these though as I wasn't impressed when I tried them), Sennheiser HD598, Sennheiser HD25-1-II, Audio Technica M50, Beyerdynamics DT770, Fostex T50RP, Sony MDR-7506, Sony MDR-V6
Headphones (If you have mod skills): SennGrado
DAP: Fiio X1, Sansa Clip+
DAC: JDS Labs ObjectiveDAC
Amp: Cayin C5, Little Bear P8 (seems pretty hard to get in Canada though), JDS Labs Objective2, garage 1217 Project Starlight
Well this list is generous and thank you guys for participating to it. If you have any other ideas to add to the list of must have gear, I'll add them to the list