Pinkward is another player of Shaco I'd recommend, he has some very good strategic plays he pulls off in terms of trickery and mind games.
Shaco is yes generally considered easy to learn the basics of, but in terms of mastery one of the hardest to be effective with at higher ranks. He's also considered pretty weak at higher ranks compared to many other champions one could choose to main. Hasn't stopped me from trying though since I enjoy playing Shaco enough, so far I've made it to Platinum III using almost only glass cannon AD crit Shaco.
He's in an odd place since if you build glass cannon like me he still can't 1v1 a lot of champs even if he catches them by surprise, is a few kills ahead and ahead in levels, you have to learn Shaco's limits so you don't suicide/feed (this is more true earlier in the game before you have several items, when you do have them it seems easier to 1v1 more of those champs, but it's still often risky). It's generally wiser to wait to catch people who don't have allies around who you ARE capable of killing, or wait to have backup before you go in.
Waiting until your allies engage is often smart, though sometimes I feel like going in on their ADC/APC and sometimes support before my allies engage is the right move, as long as your team is able (and chooses to) follow up. It may be necessary to ping your intent to go in since allies don't always seem to notice you going into the enemy backline.
You've to keep in mind enemy abilities that reveal you (Rengar Ult if you're the closest champion to him for example), as well as sweeping lens and control wards.
He's nice for split pushing if you have the kind of item loadout I take since he's very capable of escaping, and can destroy both minions and towers/inhibs/nexus very quickly, but if allies try coming with you it can be problematic since they probably won't be able to escape (if your intent was to push the lane, try for a tower maybe, and get out using Shaco's kit with a small margin of safety, during situations that would get most champions caught and killed), allies following me during a split push, or refusing to join the team and stop splitting so I could split has lost games for me in the past (they would go too deep and get caught, usually multiple times or at a particularly bad point later in the game when we needed them to live, not sure if they were just bad/tilted/had given up/were inting at that point).