First of all, this is my first Guide, so there'll be a couple of mistakes, but please tell me them so i won't do it again.

BTW i'm german, so my english isn't the best, but hopefully you'll get the Core of what i say. :)

So have fun and i hope this guide will help you a bit.

Just a tip: Even before thinking about Runes, Masteries or Items have a closer look at the champion, its statistics, its abilities and its scales.
Malphite for example. A friend of mine picked him and only knew that he is a tank, so he gave him life. But indeed Malph is an armor tank, even his E scales with armor, so investing the gold in armor items like Randuin's Omen is very viable with him.

So, what are we going to do with Lee Sin? Well, his Q,E and R scale with Attack Damage, or to be more precise with Bonus Attack Damage. Because of his passive he has a good attack speed. So actually he doesn't seem to be that Tanky DPS i called him in the title, does he? Check the stats, he has low health, and not very high armor and magic resistance. So pure Attack Damage on Lee Sin will deal much damage, but he weill die very often.
Also he only has his high attack speed because of his passive, and he only has his passive active after casting a spell. He has a lot spells, but not the shortest cooldowns, and sometimes you are forced to activate your skills in a short combination, so after your kind of burst damage you are hopeless - and then you are squishy, awesome.

So attack damage is great, but tanky is better.
So now we know we want Lee Sin to be a tanky DPS, so we can specialise our Runes, Masteries and Items around the facts we collected.

For sure there are other ways to play Lee Sin, and maybe everybody thinks different about the facts i told you, but this is my guide, so my conclusions will be used :p

So this idiot talks about a tanky DPS Champion and then has chosen 21-9-0 Masteries? WTF?!

Yes, yes. Remember, we are jungling here. How do you think an early game tank can gank? Your ganks wont deal damage, so you have a great look at the enemy walking away to his turret while you arent able to kill him - BUT ARE TANKY!

Suprising ganks have to destroy the enemy fast, so early game we need damage. Therefore i take aggressive Masteries which are going to increase our damage early game. Late game your stats base on your items, not on your Masteries. So take Masteries for your early and mid game, and there we need damage.

It's the same with the Runes, take them for early game.

Armor Penetration Marks are the best choice for us, because Lee Sin does physical damage, so early game we kill the enemies armor and deal something like true damage and it's more effective than attack damage marks, the rease they are the typical choice for an Attack Damage Rune Set.

Flat Armor Seals are great for jungling, your armor will increase with leveling up, but at early levels you need extra armor for the jungle.

Magic Resist per level Glyphs. So the per level runes are better than the flat runes, yes, but i told you that you only need armor very early, because it will get enough with a couple of levels, and the flat armor runes give more armor on lvl 1 than the lvl runes, and exactly on lvl 1-4, where flat runes work better you need the armor, so there is no need for armor per lvl runes. But there is a need for a higher Magic Resist on lvl 10 than on lvl 1. As a jungler your primary gank lane will be the mid, and who's there? The AP Carry, got it. And these runes are for the protection against the enemy mid lane. His Ability Power will raise with his lvls and items, so your protection against him has to raise, runes per lvl.

Attack Damage Quintessences. Here we take the attack damage, with the marks the armor of the creeps is at 0 for sure, so to have higher damage early is great. And even the armor of enemy champions early game will near be 0, so you dont need to take even more armor penetration. Quints for armor penetration would make sense when you want to penetrate their armor a bit late game, but then we already are the tank.

So this set of Masteries of Runes give us an awesome advantage early game, in the jungling and for the ganks.

I don't want to explain his skills here, we did it before a bit and you can read by yourself what they do. I want to explain why i max which first, second and third and how to hanlde them.

I just like to take all 3 skills at the first 3 lvls, so i do it here aswell. I start with my E spell because it deals AoE damage to the creeps and is reducing their attack speed and so finally their damage against me. Second i take my Shield/Lifesteal/SPELLVAMP so i block and get life in the jungle. With these two abilities i am nearly able to have my passive always active - deal much damage. The Last is my Q for ganking btw.

I max my Q first, again because of the early game damage. Both spells deal damage, both spells scale with bonus attack damage, so it's the best option to deal damage.

My E second, because with higher levels its slow is higher and since you are forced to jump into the enemies to deal damage a heavy CC is a great option.

The W last, because it's the only one left.

Take the ulti whenever it's possible for sure, just because it's the ultimate.

Actually it's like...
...First Skill for early game
...Second Skill for mid game
...THird Skill for late game

Q First for higher damage early game
E Second for higher CC mid game
W last because it's the only one left, and securing a teammate with jumping to him, giving him a shield and slowing the enemies heavily so your teammate can leave alive is so p0wn!

So, this is a Jungle guide, so here's the Jungle part of it.
Actually in my opinion the route you take is nearly the most unimportant thing about jungling. Lvling fast, so living long in the jungle and great ganks are more important for me.

But here is my Route.

Ghosts > 2 Golems > Red Buff > Ghosts > Gank

I lvl my E first, and i have the most targets with the Ghosts, such a coincidence!
I smite the big one, do an auto-attack, activate my E, do 2 auto-attacks(passive's always for 2 attacks), E reactivation, 2 auto-attacks, kill them with auto-attacks because of cooldowns - great.

Walk down to the 2 Golems, and go on the little one. The little one first? A combination of auto-attack, E, 2 auto-attacks, E, 2 auto-attacks, auto attack will kill the little one, and then, while the E is on cooldown, only 1 Golem is damaging you while you attack slow. The Combo again will kill the big one then too.
Acually you have to take 2 pots here, because they deal much damage.

Then the red buff, because i am lvl 2 and have my W, so my passive will be active a lot, and i smite the red buff with Iron Will active, the second W, because that gives me SPELLVAMP, so i will gain life smiting.
I guess that another pot will go down here.

Then we do the Ghosts again, and then we are lvl 3. With all abilities we can gank now. Let the mid push, throw your Q at the enemy, jump in, quick double the E for damage and slow. When your mid lane reacts good, everything is working well, both burst damages are high enough there is a kill or assist for you.

Well, after your first gank you have to take a look how to go on, you can do the wolfs, and give your blue to the mid lane, or when the enemies have no jungler you can counter jungle. I think it pretty unimportant how you go on now, just always have a eye for the buff timings, only the beginning of the jungle should be planned that way.

You actually can start at the red aswell, i would take the W at first then, but i dont want to gank at lvl 2, so i just do it later and easier with two skills.

So, this is important. You want to be a good tank, but disrupt and destroy your enemies aswell.

In the Jungle we want to start with a Cloth Armor and 5 Health Potions, getting a Wriggle's Lantern early, for early game attack damage, life steal and some more armor aaaaaand A FREE WARD! WEEEEAAAH! ..ok

Next items are shoes for sure. I prefer the Mercury Treads, as the disrupting tank it's somehow not so good when you can't disrupt because you are....disrupted by yourselve. They also fit perfect because you have armor because of the Lantern, so you have a bit protection against everything.

So mid game's opening, so we start to get tanky and disrupting - Frozen Mallet. We have armor and magic resist because of the Lantern, the Shoes and a bit because of the runes, so we need life. So at first we get the Belt for Tankyness which we finish into a Frozen Mallet. We don't need the Warmog's so fast, because we have the armor and magic resist, so the Health of the Mallet is enough for now, and the slow is awesome! With your E-Skill you nearly can stop the enemies from moving, and with your insane ultimate you can kick an enemy into your team, or a turret.

Next is a Sheen. Don't mind the ability power, don't mind the Mana, but love the passive! Jump in a fight - DAMAGE - AoE skill - DAMAGE - Slow Them - DAMAGE - Shield a teammate - DAMAGE - get lifesteal - DAMAGE.
Lee Sin has 7 skills, he can proc the Shen very often, and he should for max damage. This gives Lee Sin besides his Tankyness and CC Abilities an wesome single target damage. But be aware of the 2 seconds cooldown of the proc effect! You don't need more than the Shen, but when you are lazy and fed you can make it to Trinity Force in the very end.

So, Tank again, Warmog's. Now good and evil is splitted, Carries are fed, and some players will deal thousand of damage within' a few seconds. NOW we really need life. The order of the next 2 items, Atma's Impaler and Warmog's is situational. If your team has some more Off-Tanks and you don't need to be the super-awesome-Tank, which you don't need to be when your team didn't fed anyone heavy, get the Impaler first, then the Warmog's. When the enemy have some fed players, you are the only Tank, and you just have to survive longer take the Warmog's first. But normally take Belt-Impaler-Warmog's.

So, now we have a lot of health, still a good armor and magic resist,and great CC and single target damage, so you should be pretty happy.Actually the match should already be over by now, but in Case it isn't, p0wn your enemies because you live no matter what they do, can slow and kick enemies around. In case the match goes on finish your Sheen and get a Trinity Force.

In my opinion, a Guide isn't a "This is a strict order how to play this character!" - it's more a "This is how i play this character, hopefully you can filter some nice tricks you can use to improve your own playsytle".
I hope that this guide helped you in that way.

This is my first guide and for sure i want to improve that, so don't be afraid of criticise!

Thx for reading
Daktylus