I don't like the way DC sets fit personally. But they are solid headsets, and I have one that I give to passengers if all my others are being used.
The old Lightspeed is not the place to look. If you are looking at anything from that company, at a minimum go for the 3G series. They are a new company, and a number of old issues exist (though they do have great quick service from what I've read). I don't like the way they feel on my head either, but the 3G that I tried on are much better fit for me than any DC model.
I'm a Telex guy. I like the way they fit, fold up, and protect your hearing. I've got a couple old 3100 models, and an old 3000 model. Never a problem. I'm going to get a 50D eventually, but in your lower price range, you may want to look at their cheaper ANR models.
The Flightcom Denali is nice as well, but I must have a lopsided head, as it doesn't feel right on one ear when I tried it on.
Check ebay for prices!