Runes, items, route? I love his concept and I want to like him, but I feel like I'm gimping myself because I always become under levled even if I get kills early. Then, possibly because I'm under lvled, my damage falls way off to where I can't even 1v1 the adc anymore.
You don't.
You gank early and try to counter the other jungler than you split push like crazy and cross your fingers that the other team didn't bring in someone with a teleport or easy map presence.
Runes, items, route? I love his concept and I want to like him, but I feel like I'm gimping myself because I always become under levled even if I get kills early. Then, possibly because I'm under lvled, my damage falls way off to where I can't even 1v1 the adc anymore.
Theres only 1 way to play shaco competitive really
Snowball early then split push the fuck out of the side lanes and pray your team doesn't die
I always start with machete, 1 potion and 1 pink ward, trust me, you don't even need potions.
Start Red and Krug at the same time: when it's 0:40, place a box at the Krugs, then move to red and place two boxes there, in front of where they spawn, move back to Krug and place one more box just before they spawn. Smite them for the stun and kill them easily. Now go red, place another box under him and then kite him towards your other two boxes. If mastered you will do Krug and red without losing and life.
I almost always like to play him with AD quints, ArPen marks, Scaling Armor seals and Scaling MR glyphs. But seriously, you will find that every Shaco player uses different runes, like, every guide I look the person uses different runes. Some even use ability power, which is not as bad as you might think. I've been thinking of trying him with hybrid pen runes, instead of armor pen.
His items are really situational. The only thing that I'm always guaranteed to build is Warrior and Statikk, though some prefer Rapid Fire Cannon. Tiamat is also really good on him. And the new Malmortius.
Possible items: 
Find the sucker. Someone who trades badly while you're doing first buff. If someone didn't bring flash to lane (Low Elo issues), gank them straight after buff. Level 2 ganks are staple for most Shaco. If you don't level 2 gank, try to counter a camp. If i'm ganking, I'll take the nearest buff to the lane. If it's mid that is messing up their trades (Like a Fizz who is getting wrecked by a level 2 Xer), I'm going to hit him hard and fast.
Shaco is all about the early. Pressure, pressure, pressure. I do what is known as picking a carry. This person is someone who is farming well, trading well, and shows intelligence by level 5. I will give them the most ganks to keep them ahead so they can make up for the crappy Shaco scaling. The ONLY TIMES I don't do this is if it's someone who also scales like crap.
3)Standard route I do against non-sated enemy jungs: Buff, lane sucker, 2nd buff, wolves, back when you can afford the smite item without the enchant. If you can't and you have mana and hp then gank someone. (IF they are all over extended farm jung real quick). Boots if you need instead also works. Smite gromp, clear wolves, smite raptors, gank top or mid (which ever is easiest.) then go to the other. Get rocky bros, back, get boots and swords, go hit bot.
Disclaimer: This is under 3 assumptions of being general.
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