Hi Aaron,
Mate, you seem to be well on your way and have addressed a lot of the issues needed to get a pleasing result.
I'm still undecided about the '500 rule' and crop factor as the focal length of the lens is not increased, rather that the FOV is decreased. Whatever, it is still better to be conservative with your exposure times and take multiple exposures and stack them.
If you aren't aware of the stacking process have a look here...
http://deepskystacker.free.fr/english/index.html
DSS allows you to stack multiple exposures while using a lower ISO to hopefully keep your noise in check. It will also allow you to use shorter exposure times and thus reduce the chance of star trails. The theory is that multiple exposures with lower ISO and shorter exposures will allow you to capture the same amount of light without the noise and trailing.
As renormalised suggested I'd turn off long exposure noise reduction in the camera settings as all it does is take 'Darks' and process them in camera while loading up your camera's buffer and slowing down the whole process.
I don't know about Canon but my Nikon still takes dark frames at ISO1600 or higher even if I have noise reduction turned off. Like yourself my maximum ISO is now 400/800.
And as I'm sure you are aware taking the photo is only the beginning of the process.
What Post Processing program do you have? Most of them allow you to re-size your pics and I'd suggest something like 1000px on the longest side and then 'Save as' at as close to less than 200kb as you can for posting here.
If you click 'Manage Attachments' under 'Additional Options' below where you are typing, it will allow you to upload the saved shot from your computer.
Keep experimenting and keep posting for comment. While I doubt that anyone knows it all, most of us have picked up little things along the way that may be helpful.