my bad about the maxing out level, see thats the thing working to max drain is important to but in my opinion dark wind is more important, for starters u can get stacks jst buy hitting it on a couple of champs and running away, and secound u can harass from alot of a further distance than drain especailly early game which means more lane control for u which is want you want, becasue chances are they will recall once and lose exp, which can be the difference between winning and losing. About sourcers shoes i dont think thats important because in my masteries as u can see u have a magic pen of 10 plus void stuff = 50 magic pen, which i believe is enough since their is no more than 2 tanks on a team so too much penetration is a waste since it goes to nothing, mejais is definately important because ***its are easy to get with fiddle since his dark wind is bouncy so u can counter attack and get 3 stacks from practically ur dark wind that can bounce around in a team fight, as about dieing thats true that u will lose a third but with a good team and if your a good player u shuldnt be dieing much, i have reached a couple of times to 20 stacks not jst with fiddle, but also with tanks (health stacks forgot wat it was called) and also as and ad (sword of occult) but with a couple of champs, jst depends on ur team ofcourse and how u play, for me it is my first choice for fiddle but well every1 has their own opinion though thank you for commenting it is highly appreciated and more comments will also be gratefully appreciated :)

Interesting choice of abilities on leveling. I'd work to max Drain first with a point in terrify early game. (Also you can't max anything by level 8, 9's the earliest) For survivability, drain is great and it does a ton of damage anyways. I'd also go Sorcerer's shoes for magic pen instead of a bit of CDR. Mejai's Soulstealer is good if you're getting a lot of kills/assists and you aren't dying. Otherwise it can be encumbering in a sense, especially with losing a third of the stacks when you die. As for masteries, things look alright.
Not my first choice for Fiddle.