Just gonna churn out some generic suggestions to hit those #ChallengeOfTheWeek's :3

SALES:

http://www.tf2outpost.com/trade/22808240 Offered + sweets (~2 keys) on a NnB Nappers (17 keys)

No overpay, 17 - 2 = 15

Histories:

http://www.tf2outpost.com/item/440,3010085070,644,5

http://www.tf2outpost.com/item/440,3010131964,248,5

http://www.tf2outpost.com/item/440,3012784463,644,5 -> http://www.tf2outpost.com/item/440,2988621660,439,5

Sold for Orb. Fire Pith Helmet (Outdated at 1.1, mini at 17 keys)

17 * 0.9 = 15.3 (rounding to 15)

Pith Mini:

http://www.tf2outpost.com/trade/21654778 Sold for Stormy Stuntman (20 keys)

20 * 0.9 = 18 keys

Histories:

http://www.tf2outpost.com/item/440,2989904681,439,5

http://www.tf2outpost.com/item/440,2830569137,255,5

http://www.tf2outpost.com/trade/21380974 Sold for Bubbling Bonnet (15.5 keys) + sweets (~2 keys)

17.5 * 0.9 = 15.75 (rounding to 16)

Histories:

http://www.tf2outpost.com/item/440,2989904681,439,5

http://www.tf2outpost.com/item/440,2801760068,100,5

16-18 on the Cockswain.

Let it ride.