Hey ICE9, got to the discussion a little late . . .
If I were starting up right now, I would pick up a Performer Premium. At $350, it is at the top end of your price range, but it's a really good cooker. You can grill steaks, you can smoke pork butts, there are a TON of accessories that you can pickup down the road to make it even more versatile. Best of all, they last forever!
I almost always use the small Weber chimney starter. Even if I'm using my Vortex, I just dump the hot coals on top of a pile of cold ones and wait 10-15 minutes.
As far as charcoal, I've always used Kingsford Blue. But I know that a lot of the gang here prefer other stuff. As a friend of mine once said when his brand of bourbon was not available, "It's all good."
Another option, and one that's working for me, is the Weber 26.75 Kettle. There's no cart, but if you're cooking for a crowd, it's definitely the way to go.
The biggest thing is to get a fire going, and soon ! ! !
BD