Alright, think there's enough info to price this now.

Hat the first (sorted chronologically by owner)

http://www.tf2outpost.com/trade/9701193 B/O 4.5--offered it on a latern guad over here, was accepted but hasn't happened yet (counting overpay that would match B/O fairly closely http://www.tf2outpost.com/trade/9257817)

http://www.tf2outpost.com/trade/9697341 Sold to above for smoking lucky shot (~2 buds?) + 28 ref (~6.5 keys) + diamond botkiller wrench (5-6 keys) + strange beggars (blegh) + some miscellaneous solly items. Other sweets may have been involved, but overall a pretty low sale, wasn't even close to their 5 B/O. They seem to have been aware of this, though (http://www.tf2outpost.com/trade/9700908)

http://www.tf2outpost.com/trade/9682973 Sold to above for holiday headcase?

Above trades all happened over a very short time period, so bp history isn't terribly helpful, but outpost trades seem to correlate the trades

Hat the second (sorted chronologically by owner)

http://www.tf2outpost.com/trade/9695690 No B/O, very new. Offer of 13th hour sack (~2.8 before overpay)

http://www.tf2outpost.com/trade/9469040 B/O of 3, sold to above for beams outdoorsman (~3.2 before overpay?), and they added a fair number of keys (though no more than 1 buds worth) if their pack history is any indicator. http://backpack.tf/id/76561198049769746?time=1364022000 -> http://backpack.tf/id/76561198049769746?time=1364108400

http://www.tf2outpost.com/trade/9467954 B/O of 3 as well, sold to above for indeterminate amount

If I missed anything let me know