What goes into answering that? Most of the others seem like they could be supported with hard data, but it's unclear to me what a 'risk' is in this context (I mean theres a risk that a skin will be unpopular, but that's true of every skin) and how one could determine if it's worth it while still being responsible with the skin teams time.
Hi~ I'm one of the two product managers/producers on skins (SuperCakes is my boss). My job is basically to answer all of those questions above. The question about risk is particularly challenging, and it's probably the one that requires the most general insight into our players, global tastes, what's resonant in pop culture and media, and just gut calls. As an example, Pug'maw was a risk. We decided to make him an actual dog--that was a controversial move internally, and players were also divided. It was risky because he hadn't had a skin in awhile at the time and the art style was very polarizing--but it was mitigated by releasing it during April Fools, where that sort of silly skin could also be embraced. But we wondered if it went too far. It turned out to be the right call to make, but as with all risks, you won't know until the very end.
After doing this for awhile, you start building up a pretty good gut to making these kind of calculated risks/gut calls--but you know, we're human so it's not a science or anything ^_^