I find it a problem when you have 2 UI designers and cannot come up with a great design on day one. Your new design isn't spectacular either. A great resource is to look at the designs of all of your competitors and understand what is great about all of them.

Also $50 for an icon is very cheap. At that price, I'm not sure how it would motivate any good designer to spend even an hour on a design. I usually pay $150-$300 per icon for my apps (smartieants.com) and I find it barely enough to keep the designer motivated.