Thanks to Foamy for the help on this suggestion. 1 of 1 in existence. Strange. Not planning on selling it. Let's do this :)

Sale 1:

Sold in a 1:1 for a Morning Glory Outdoorsman (50 Keys)

http://backpack.tf/profiles/76561198061568403#!/compare/1477440000/1477526400

http://i.imgur.com/l4xwMvR.png

Outdoorsman is only barely outdated and I couldn't find a mini, but there is 1 seller on OP with a B/O of 50 Keys

http://www.tf2outpost.com/trade/28567338

Outdoorsman = 50 Keys

Sale 2:

Sold for a Death at Dusk Barnstormer (60 Keys) + 3 Keys

http://backpack.tf/profiles/76561198058928752#!/compare/1475625600/1475971200

History of Barnstormer:

http://backpack.tf/item/3356912760

Barnstormer is outdated, so it needs a mini.

60 + 3 = 63 Keys

Stetson = 63 Keys

Mini for Barnstormer:

Sold for a Duped Haunted Ghosts Large Luchadore (54 Keys) + Strange Pro. KS Tomislav (6 Keys)

http://backpack.tf/profiles/76561198112509663#!/compare/1475366400/1475452800

History of Luchadore:

http://backpack.tf/item/421680783

Tomislav last sold for $14.79 (Oct. 28, 10 p.m.) on the market.

http://steamcommunity.com/market/listings/440/Strange%20Professional%20Killstreak%20Tomislav

14.79 * .85 (for the 15% tax) = ~12.57

Keys = $2.16

12.57 / 2.16 = ~5.82 Keys, which rounds to 6 Keys total.

Tomislav = 6 Keys

Luchadore is duped, so it needs a mini.

54 + 6 = 60 Keys

Barnstormer = 60 Keys

Mini for Luchadore:

Sold with a Unique Schadenfreude Taunt (0.85 Keys, which rounds to 1 Key) for a Green Black Hole Connoisseur's Cap (55 Keys)

http://backpack.tf/profiles/76561198166805884#!/compare/1471478400/1471564800

History of Connoisseur's Cap:

http://backpack.tf/item/1932020652

55 - 1 = 54 Keys

Luchadore = 54 Keys

Let it Ride!