Items

Individual items
Starting from the bottom of the list in the Item Sets tab;
(Summoners rift only, and items that most Shaco would build.)
Infinity Edge ; Yes, I like this item. It is expensive, but very strong and almost considered core on AD Burst/Δssassin Shaco. If you're really ahead, go ahead and get it second item.
Trinity Force ; A huge gold sink for small amounts of a bunch of stats. Don't get me wrong - I like this item. But it is a HUGE goldsink. Getting it later is strange and I rarely recommend it as a rush either. Same as IE. If you're massively ahead, go on and get it. But you might as well pick up BOTRK, Shiv, or Hydra over this.
The Bloodthirster: Usually you'd pick this up during mid->late game, if at all. Works quite well, I find if you've got a lot of attack speed, and are ahead enough to go for another damage item. The shield helps your dueling, and gives you damage and life steal. No real downside, fairly costly.
Frozen Mallet: Maybe EXTREMELY situationally - overall? No. Don't bring this up to me.
Ravenous Hydra: Yes. Yes yes and yes. Aoe, lifesteal, health regen, wave clear. All things Shaco loves. Helpful in splitting, helpful in teamfights. Perfection, god bless u buy this item. Usually early game.
Essence Reaver: No, kill yourself. Yes, cdr and lifesteal are good, but you shouldn't be buying this.
Blade of the Ruined king: This is a good item - however after the nerfs, it's no longer rush(Like Hydra), but more of 5th/6th item. Maybe earlier if you really need it, but not 1st/2nd item(after jungle item)
The Black Cleaver: I enjoy this item - but I usually get if after it's gotten so late, I'm selling my jungle item. Really beneficial at that point, since most will be stacking armor to try and survive the ADC's.
Phantom Dancer:I like this item, but shiv is usually a better pick up, better for dueling/wave clearing with. Not bad, but you probably won't be getting this very often.