I've just realized that my dislike for the general Gust of Wind/Boss's Orders effect might be influenced by the fact, that I've never played in a format that did not feature Pokemon EX/GX/V. The most frustrating scenario in which Boss's Orders is used, is in the classic "if they have it, they win, if they don't have it, I might win". In a "regular" game, that would only happen if both players are down to a single prize, something that's not going to happen in every game. In a format that's mainly EX/GX-based, that's going to happen way more often, and not just due to the fact that's it's just mathematically two times as likely, but also due to a number of other, more subtle factors. With triple-prize Pokemon, that scenario is going to happen constantly, in back-to-back games. To "flatten out" the randomness you need time - that's why we play Best of 3 or Best of 5 games. The shorter the game, the more random effects have a larger impact over skill.