I know that probably seems ridiculous, but it's been in the back of my mind before. This year I thought to ask my boyfriend about it, feeling a little sheepish!
I told him I felt just a tinge of sadness for the Man when he raises up his arms. This is quickly overshadowed by the awesome event of the burning itself...but still, just for a few moments, I have this strange bit of empathy for an non-sentient object...it's like we're old friends that have shared so much together and now it's time to say goodbye. Maybe it's just a subconscious reckoning that the event is nearer to it's end than to it's beginning...but still. It's an odd little feeling, if not misplaced, and seems centered on the Man himself.
My boyfriend's answer? (if I'm not misquoting him) "NO! I never feel sorry for the Man. He wants to burn, it gives him his power!"