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To Piper11- iv'e yet faced against a Vladimir top lane so if i do i'll adjust but untill then ill stick to what i have :) & Teemo does put a dent into Tryndamere but i almost never lose to a Teemo because he is squishy and can be taken out quickly without too much done to you IF planned correctly. And his poison can kill you IF Undying Rage isn't used at the right time with Bloodlust following it.
You should consider replacing the Wriggle's Lantern because it scales off late-game, and your job isn't to be warding :). It's the supports.
Building the Wriggle's Lantern is entirely up to you, but in my honest opinion, this item is more preferable for a jungler, rather than an AD solo top. You're better off with two Doran's Blades as it IS cheaper, and gives about the same output, along with 160 HP. You can buy Health Potions and Sight Wards if you really need it as well, with the extra gold.
Also, try naming your guide to something like Tryndamere - "blahlarhgneairh". Something so that people would know what your build is, to attract viewers.
Good aesthetics, however, you're on the right track.
I'll vote when you put some more time into it. Good luck!
Consider building items such as Hexdrinker and Mercury's Treads when fighting against AP top lanes. Also, consider switching your runes to flat ad and MR/lvl. The runes you have now are ok, but having the AD flats will allow you to farm better , and the MR/lvl will be effective in almost every game. Also, remember that Trynd's whole playstyle revolves around the auto attack, not abilities, so having -CDR runes doesn't mesh that well with his kit.