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On the topic of building "support" Kayle, I say that you can pick up some of those items and explain very well why you can. I'm not saying "Well give up on your end game" I'm saying that something such as Heart of Gold or Aegis of the Legion can help you get back on your feet and into a better groove. While this won't directly increase your damage output at the time, it will make you tankier in order to live to actually DPS something. I will take an Aegis over a Guinsoo's when I am behind without a second thought. Being underleveled and behind farm changes the game and unless you change your game in response, you will not get ahead.
The Offensive masteries I have laid out help her gank well and jungle well, and you never truly build her support. She does enough damage with her base values and Wriggle's Lantern to cut through a lot of the cast unless they're really far ahead of you. If you don't have the dual penetration, your ganks and jungling speed will certainly suffer and no items you build can make up for that.
@Tina: As stated above, I don't really see a need for the 9 utility, either. You don't need the mana because she's really streamline in terms of that and don't need the movespeed because of your boost on the heal (more helps, but not necessary). The armor, however, will allow you to have a higher life jungle which I value over 2% movement speed and buff duration (that she doesn't need because she has a ranged slow and is mana efficient). Leveling Divine Blessing over Righteous Fury severely damps your jungling speed and ganking damage. You don't really play Kayle to be a sustained jungler, you play her to provide high damage awesome ganks at any level after 2.
Perhaps I should make the point that you're not going "support" Kayle if you're behind, but that one or two of these items should be built to get you back on your feet. I don't recommend building her full support or full tank in most circumstance, but realistically getting a support item or two when you're 0/5 and 4 levels under is going to help infinitely more than a Pickaxe or Blasting Wand.
I tried Trinity Force and it was good, but junglers have a rough go with expensive stuff unless they're fed. So you can't really get a Wriggle's and then TF, you'll have it at like 30 minutes in a normal game which is useless.
Personally I enjoy having Trinity and Guinsoos on Kayle, keeping stacks high isnt much of a problem once you have some CDR and in fights this item makes up for the trouble with ease.
I wouldnt buy it first though.
Trinity is great, it provides another slow, which is important for chasing faster targets, more speed, simply great, very nice burst dmg through Sheen, I actually did burst down a Kassa time and time again on my last game :D he thought he could jump on me for some harass, but I tought him a lesson.
I also tried On-Hit Kayle, also pretty good, but if you are behind its not that good anymore imo.
Tanky Kayle evenly great, I dont know how to suck with Kayle :D but full AD I find to be bad.
Of course it can work, but its not to Kayles strengths at all, she´s little more than a squishy AD Carry with poor range and 3 seconds time to rage, unless CC´d, little better than AD Teemo, but not much.
AD build also costs way too much, most AD Items have no AS Boost, Hybrid or On-Hit, even Tank is much better.
God I love Kayle, too bad I cannot take Surge instead of Smite to jungle, Surge is pretty much awesome with Kayle.
I remember having a double kill at lvl 1 with Surge once, vs Vayne and Sona :D
Definetetly try it out if you play Kayle outside of jungle.
In terms of Masteries, Im using the same, but with 9 in utility, dont feel like I need this defense with Kayle.
Im also leveling Heal over Flame Sword, maxing the latter at last or in between, but having a stronger heal really comes in handy, strengthens your sustain and makes you a live saver and assists in tower diving.
Once you fall behind as Kayle, you can take on the support role, but I dont think this is pretty much recommended.
Build little more tanky and dont neglect AS Items, you still can dish out quite some dmg if the game drags on, use oppurtunities to farm whenever you can.
AS is most important to deal some dmg and be of use, if you fall behind, build more tanky but remember to buy AS as well.
-1 for now
Very pleasant guide, I'll consider doing this even if I think Evelynn will remain my favourite jungler
EDIT: What do you think about Nashor's tooth on kayle? Same as Malady or Guinsoo's?