Point 1)Sry dudue your guide only gives 30% cdr.
Point 2) Cut Down + Overgrowth + Life ablity items a bit pointless for a good work together ?
Point 3) Font of Life is a weak ablity and brings yourself nothing maybe sure if you mark someone but its more for support stuff and at this point you will be more usefull with improving your own defense.
Point 4) Lyndras Tournament is interesting to build but expensive and brings you only the buff for the stunning hit 1 time if your fast enough the slowdown just take 2 secs.
Point 5 ) It makes more Sense to build nashor than wits end if you need attack speed couse you already used the ablity power from the jungle item and you also get cdr very quick.
Point 6 ) Dead mens plate sure can be good one but whats against ap ppl that do more dmg than most ad that you can counter.
Point 7 ) Press the attack. Ok maybe works fine with the Q ;) but if you go without ad stuff just with hp stuff its complete useless to play that in this build.

My Changes for you: Choose Coup de Grace. 2. Build Shild bash it Improve your shild defense that you just improved by hp its an strong rune and do high diffrence.

Your Item stuff: If you wanna play with Trinity Force Change your ap jungler item into AD. IF you wanna play with Titanic Hydra Change your Lyndra into Mormelonikon. Your Jungler you need boots and slow cdr rate its not often possible to build 6 items in a match and wits end doesnt rly carry against ap ppl. That means change it mercury boots.

Go for legend Alacrity than tenecity. At least build up an defensive item like zekes convergance. So now you have 40% cdr very late and your defense is weak but your shildpower is strong....i still think that these item combinations are to expensive and takes to long time to build them all up together and you have bad cdr balance. Not a good way to build up.

If you go for AP stuff build lich bane than trinity force. Couse the diffrence is the hit after skill between ad or ap and to improve with ap is an good point. Check my guide ;).