Well, feeling overwhelmed before you posted was apparently nothing compared to after everyone responded.
Everyone likes headsets for different reasons. Price, fit, form, and function. It's all a very personal thing. You can look and look until your blue in the face. However, as Ron said, "it's your head" so find something that works for it, not your buddies. Also, decide what you want on it; ANR, dual volume, iPhone/Droid integration, bluetooth, color, etc. You have a
great budget, and there are a lot of options for that price.
Borrow others headsets. Most of the pilots that don't have their nose up in the air to everyone will let you use theirs for a flight to try them out.
Just remember, that in most cases, you get what you pay for. However, any headset over 600 bucks, you're paying for their name. Any headset for 100 bucks, is just that, and nothing more.
I won't pitch our product to you, but we have great options as well with all the things you need, and some that you want.
A link to us:
The Squawk Shoppe
Good luck, and enjoy it!!