Personally I absolutely love Winn ...... because I hate her character so much.
As soon as I see her in an episode I know I'm gonna enjoy it because she'll leave a lasting memory for me as to why I dislike her so much. Louise Fletcher is such a beautiful actress because she makes you forget you're watching a TV show and makes you absolutely want to step into an air lock and blast yourself out into the vacuum of space just to leave her presence.
yup. it wasn't until the final season that I recognized her as Nurse Ratched from One Flew Over.... damn fine casting, and she's an impressive actress, it takes SKILL to make people hate you like that.
I always got the impression that everything Q did was simply irritating. Winn made decisions that actively risked people's lives because she was looking for career advancement. She was actually a threat.
Also they kind of knew that Q wouldn't actually allow anyone to get hurt because he probably wasn't allowed to.
Q did things that were ultimately to the benefit of the characters. Picard is a better person from Tapestry alone. I wouldn't even call Q a villain. Antagonist, yes, but not a villain.
I thought the idea there was that the Borg were already on the way and him doing that gave them a chance to prepare. Then they reinforced that idea with First Contact and Enterprise, because at that point they didn't know how to write a series without the Borg.