For prettiest items and quality-not-quantity: First Place to Riley for a Hannah Montana Soundtrack
For most variation of items (shirts, shoes and shorts) : First Place to Nikolai for a Kinderegg and 1/2 shares in an underwater digital camera.
For most creative item (Sister for Sale shirt) as well as most items per dollar spent (he had the most items but gave Nikolai an item upon getting back home): First Prize to Bridger for a Kinderegg and 1/2 shares in an underwater digital camera.
Overall, Nikolai was the winner for sure. He found all his pieces himself, chose items that matched and got the best variety. I will be better prepared next time and do it all in one day with prizes ready. Maybe I'll preplan catagories...