Well, I've got the 350D, which I love, and after seeing the 400D, I'm OK with not having the latest and greatest model. Sure, a 5D would be nice, but the 350D is enough camera for me now. As for lenses, I started with a 50mm f/1.4, and I quickly learned how much using a flash just sucks (more on that later). After the 50mm f/1.4, I picked up the 200mm f/2.8 since I wanted to get some pictures at my dad's graduation. The 50mm is an awesome lens, but if you need reach, it isn't the lens for the job. But the flip side is that if I want to take a picture of something large, the 50mm isn't too great there either if I can't take a few dozen paces back. So I picked up the 15mm f/2.8 fisheye and created an automator workflow to defish images in seconds. No need to open an image editing application. I keep all of this in a LowePro Slingshot 200AW, which I am a big fan of.
What do I regret? My 430EX. I've got lots of fast glass, but I fear one day it won't be fast enough, so I keep this around. I should have waited for one to shop up used at a good price, but didn't.