It might be a better idea to have your resistor before the diode to limit the current. I think having it after the emitter causes some interferance with the transistor turning on, although i could be wrong. Another idea is that you could just switching to a MOSFET driver they're a bit easier to work with.
What you should do zach is move the limiting resistor to the collector of the transistor (in series with the LED), and use a resistor to feed the base of the transistor. That's how it's normally done, and for good reason!.
Maybe this little circuit built on a small piece of vero board 7x8 holes could power your superbright led as I tried it out with 5-10,000 mcd white led's and it nearly lit up the workshop, I found by putting limitting resistors on each led the brightness only go better. So if you want any futher info let me know dude cheers Bryan1