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Nice looking guide I'll give you a +1 gladly, I build Trundle very similarly. One suggestion I have though, have you considered a Trinity Force? Sheen will proc his Q, which gets spammed alot. I've found it to work very well, I get Frozen Mallet if I need more hp to tank better, Trinity Force makes him more off-tanky.
I find that in Twisted Treeline, you should have a ranged carry, and two off-tanks/tanks. Also the two tanks need some good CC. Pillar is his only CC and it's pretty situational. I find that getting a frozen mallet assures that your opponents can't run, also the HP keeps you beefy.
If all three of you are squishies, someone like Annie could solo your team with preparation, this makes for a bad game.
You obviously can't have both TF and Frozen Mallet in the same game, way to much gold. But a Sheen may be a decent item to get after finishing the build, I also started finding that most of my games I finish this build in 20 minutes not 30. Wasn't paying much attention to that until now. I am definitely adding a Sheen to the build though, good suggestion.