It seems to me that the right time would be whenever it will win you a match. Also, I would argue that doing simple/marginally difficult things perfectly when it actually matters is more impressive than doing really complicated things when there's nothing on the line, not only because of the level of pressure involved, but because it demonstrates flexibility and mental agility in addition to manual dexterity.
Again, I never said that you aren't capable of impressive things. In terms of just manipulating a character on the screen, I think you very well could be "more technical" than PC/M2K/et cetera. I just think that they do more impressive things within the context of actually playing the game well.
I think a lot of this comes from my preoccupation with music (my day job, so to speak). I see a lot of videos on Youtube of guitar players who basically just move their fingers really fast and play complete drivel. Compared to somebody like John McLaughlin, for example, these "shredders" do nothing for me beyond just provoking a sort of knee-jerk "OMFG" reaction that quickly turns to disinterest. I suppose this couldn't really be considered a proper analogy because music is so subjective whereas Smash is simple black and white win or lose, but what I'm trying to say that is that McLaughlin's playing will always be more impressive to me because he uses his formidable technical facility to the end of actually communicating something of substance to the listener, rather than just trying to be as flashy as possible.
It's a hell of a lot harder than pushing buttons really fast.
P.S. We should play at Smashtaclysm and why are you using XIF's sig?