Heya, jungle onetrick here, i'll break down the jungle role really quick in case you're a little lost or if someone reading this post is new to the game
Basically, the purpose of jungling is to flank lanes and secure the big monsters (Baron Nashor, Dragons, Rift Herald)
To do this, you farm monsters for the gold and XP to stay on the level curve with everyone else
That's the summary of your purpose. Stay on the curve, attend to lanes, and get objectives.
Now we get into the questions
1: For jungling, you can start one of two items;
Hunters Machete, or Hunters Talisman 
Talisman is great for AoE-heavy ability casters like Kayn or Rammus, and provides a burn effect to monsters + self healing upon the damage ticking to the monsters (but not lane minions or champs) upon damage.
Machete is best for super auto-attack-heavy champions like Master Yi, Udyr, Trundle, etc, providing a minor amount of lifesteal-when-hitting-monsters and some additional monster-only bonus damage on auto attacks only
Taking one of these two is borderline mandatory, because it grants you a massive XP bonus when killing monsters. Without it, you will not only fall behind in levels and have a slower clear, but will also lack the sustain from either option
These 2 items will be combined shortly, so you'll get both's effect anyways, and when combined with an extra 300 gold will become either 
Skirmisher's Sabre, or Stalker's Blade
otherwise known as Red Smite, and Blue Smite
^This^ leads to...
2: Different Smites
Challenging Smite is the duelist's smite. Champs that love to go ham or go home will use this best. Master Yi, Xin Zhao, Graves, etc.
Chilling Smite is the catcher's smite. Champs like Udyr, Evelynn, full damage Kha'Zix perhaps. Assassins and champs that need to keep up with you or outrun you to be effective will take this
Challenging Smite will reduce damage that you take from the champion you smite, as well as granting auto attacks a burn damage, though incredibly small, to the enemy. This is mostly used for the damage reduction. Champs that don't need any assistance to stay on top of a champion will adore this, obviously
Chilling Smite will upfront damage the enemy by a small amount and also slow down the enemy, stealing some of their move speed, and granting it to you temporarily. Tank champions, and bruisers that lack in an ability to keep a champion still enough to combo down will take this one the most.
Once you upgrade to either Challenging or Chilling smite, you can choose from 4 very gold-efficient upgrades, that still grant all the stats from the jungle item components. These enchantments are as follows
Warrior, just a crapton of AD and some cooldown reduction 
Bloodrazor, high attackspeed and a strong on-hit effect 
Runic Echoes, which is just bootleg Luden's Echo but meh 
Cinderhulk, aka Sunfire Cape + bonus health for building health 
As you can tell, these cater to the 4 major champ types. Casters, Autoattackers, Mages, and Tanks.
Build the one it reccomends, unless you're breaking the meta or contouring to the team's needs super super hard.
3: Yes, quite obviously. Look at sites like op.gg in the jungle to get a grasp on what's meta now, but don't worry about meta-slaving. I'm a Vi onetrick, and she's a teir 4 champion. If you love a champion's playstyle and can make it work without sacrificing important things like jungle clearing or ganking, you can practically play any champ. I've seen people make disgusting champs like Yasuo, Blitzcrank, and Twitch surprisingly effective in the jungle, but again, use common sense. Don't go full movespeed and attackspeed Janna if you want to have a good time and not have a full team flaming you for doing stupid shit
4: Runes are champion-to-champion. They're not always going to be the same
Most runes completely do not effect your jungle clear, as the only rune that procs on monsters is Fleet Footwork i believe. If you're Graves or Twitch, rejoice to that fact. Otherwise...
Basically, you want to AVOID taking runes that rely on poking people down like Kleptomancy or runes that are most effective in duo lanes like Guardian. You may still use guardian, but klepto is pretty much one big no-no for jungling
I've taken the liberty of looking you up on op.gg and since you play Kayn a lot, i'll supply a rune page for you, as i also play him
Before the game starts, you will want to decide on a form to pick. If you're in draft or ranked, use the enemy's team as a backbone for this. They have 3 melees and two of them are tanks? Prep for rhaast form. They have 4 squishy ranged? Shadow form is fine.
If you're going red form:
Precision Tree: Conqueror, Triumph, Legend: Tenacity, and Coup de Grace is standard.
Pair with Sudden Impact and Ravenous Hunter in the Domination (red) tree
- Conqueror is a late-game long-fights rune. It's mehhh until 20 minutes, but you'll be doing the most work as rhaast PAST that point.
- Tenacity means that you don't get stunned for 7 years. It's important, since almost all of your ability to survive relies on you dealing damage by casting spells, which you can't do if you're stunned
- Triumph is just OP.
- Coup de Grace is the only decent teir 4 mini-rune
- Sudden Impact will proc when you Q, and lethality/armor pen is crazy good on caster champs like Kayn
- Ravenous is basically just your passive but more of it. Take it always on rhaast. This is pretty much mandatory with how good it is.
If you're going blue form:
Domination tree: Electrocute or Dark Harvest (Electro is easier, DH is still okay to take though), Sudden Impact, Eyeball Collection/Poro Ward, Ravenous Hunter or Relentless Hunter.
Pair with Absolute Focus and Waterwalking in the sorcery (blue) tree.
- Domination is the murder-y rune path. It's great for assassins, and electrocute and dark harvest are just bonus damage for your damage
- Absolute Focus gives you a fuckton of bonus AD when you're full health. Use your E spell on walls frequently to stay very healthy on Kayn.
- Waterwalking makes you run fast through river, and also grants AD when there too. Makes scuttle crabs easy, and makes running through the map super fast lategame when you are SONIC THE EDGE-HOG
anyways i'm ranting.
These are easy enough to understand, but basically look up runes for a champ before you pick them up, and feel free to experiment! Turns out, Hail of Blades is disgustingly good on Vi, but everyone took electrocute or aftershock until recently.
Thus, I've addressed the points asked in the thread, It's taken quite a while, but that's generally all you NEED to know. Now here's some stuff you might WANT to know:
Here's some quick tips:
Be aware of your jungle camps respawning every couple minutes, don't leave them out for too long because they respawn a set time AFTER you kill them, so for maximum XP and Gold efficiency, always be clearing them when you're free to
Ping TONS when you want to make a play. If your laner decides to pansy out and doesn't want to commit to the gank or a late-game fight, then don't go in. You don't need to die for no reason if the team's being uncooperative
Don't worry about dying for a GOOD play, but don't throw yourself into fights unnecessarily.
Only commit to a gank (when you flank an enemy from the jungle) if you're very very confident cannot go wrong. If you THINK you MIGHT be able to fight the 12/1/10 Irelia top lane when you don't even have your Warrior enchantment (jungle upgrade), if you just play it perfectly and she somehow loses her internet connection, you shouldn't take that kind of risk.
Ignore hard-losing lanes. I know, this one is the most controversial and hated rule of jungling (by laners, at least), but it's important. For an example, If the enemy top is huge because your top is an idiot, do you really think that giving him a kill will make him NOT keep feeding?
The best course of action in that game would be to snowball your other lanes into an unbeatable powerhouse, get yourself fed as well, and then 4v1 that hoe with the fury of a thousand suns and a disgustingly fed ADC to melt them down. If the ally losing laner is actually good, they might then have the opportunity to regain their footing and become an actual minor threat instead of free gold. It's funky logic, but it's the most effective strategy
Finally, don't get into an arguing with those kinds of laners that are too dumb to know what you're doing. If someone is being a twat waffle, ignore them and play to your best ability. They're ping-spamming you "?" marks because you aren't camping their lane for 30 minutes straight? Mute em. They're trying to attack you for taking like 3 minions to help shove the wave under tower? Mute em
PS: This isn't a full-on mandatory requirement, but wave management is really important. Just because you can take some free minion gold from a dead lane doesn't mean you always should. If the enemy has more minions than you, let the wave push in. At most, trim it so that there's still 1 or 2 full health minions more than your wave. Setting up a "freeze" like this for a smart laner is the best way to climb ranks if you try competitive mode and hit silver or above.
I'll stop now before i make another 6 pages of advice, but just take in however much of this as you can and you'll go pretty far. If i had this assortment of advice when i was bronze 2 i wouldnt've stayed that way for a whole season :P
Thanks for reading, and best of luck in your games!
-AetherArising, 222k mastery points 
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