If each victory was so hard to achieve it would get boring, I think. Isn't it just how overplayed ST was, what bugs you? We had our hard fights. Elfman vs Bacchus, Wendy vs... that Wind God Slayer. And we had a bunch of losses. And a bunch of easier victories. It all evens out, to me.
No, because if ST was overplayed, then it would reflect back on every singel guild they were above (the entire magical world).

And about all the loses were pretty cheap in my opinion, with as i recall it only being Grey who lost a fair fight, all the others were rigget in some way, og just completely unfair.