Yes, having a recent icon win is definitely awesome! From me the winner was from July so it's at least not from January or something but still there's the implication that i got worse, so, I would have loved to get a new winner like you did. (then again I get why an older icon won, cause I had a huge iconing slump through the rest of the months and didn't even post most of my made icons properly so maybe that's the explanation x) )
I don't see any ugly icons in your poll though, I think you're being too hard on them! As for your last question, there are always benefits in analyzing why people might have voted for the icons they voted for, but in the end you can only guess (some votes are based on personal taste and some on execution quality, and you can't be sure if an icon wins for color, composition, texture use, brightness or something else) so it's best not to let it affect your style too much. I think all of your work is awesome as it is tbh :)