I have trouble recalling Shakaar freely. I think that goes for his character for most of his time on DS9, as well as this episode. I appreciated what the writers were trying to do with him, but I just never found him particularly inspiring. I was glad when he disappeared again.
BRING BACK BARIEL!
I love a bit of Winn usually but the use of her here isn't thought out properly. She's just the obstacle in the way of getting Shakaar into power, and it's all a bit contrived.
I loved Kira's old friends though. They were far more interesting, and I loved that they later reappear in The Darkness and The Light.
And O'Brien's story, while funny, is symptomatic of a few of Trek's B or C stories where other members of the cast are occupied with something frivalous whilst their friends are caught up in all kinds of danger. Live together, die alone perhaps?