Most of the comments here are going to bash her, although I suspect the silent majority of Adventures in Odyssey listeners likes or loves her character.
I have a more balanced perspective on her, I think, than most people likely do. I think she was a good idea for a character, but that ultimately, when you consider the
Green Ring Conspiracy as a whole, she might have fallen short of the mark.
Before
The Green Ring Conspiracy, Connie's character development had sat stagnant for some time. I repeatedly stated that she needed some real, tangible character development, and that there would be no point in keeping her around if they weren't going to let her do something. Not just
lip service to character development -- but actual changes and growth.
At the beginning of the
Green Ring Conspiracy, in the first scene with the art class, I realized that either the Odyssey team had heard me, or they had thought the same thing separately, because they were doing what I wanted to happen.
In that scenario, Penny Wise emerged, and I think served a valuable role as a character -- serving as an effective foil for Connie's lack of self-confidence and indecisiveness, and generally keeping her on the path to progress. She was practical, sensible, and while quirky, not overly so; it didn't drown out the overall theme of the character.
If it had remained at that, I think even the critics, the people that hate on her now, would say that they liked her as a character. The sub-plot with Dr. Trask's false teachings would have been enough material for Connie to deal with, and the story could have still gone along in a sensible manner.
Unfortunately, it didn't. Wise met Bassett, and thus began what is possibly now the most infamous relationship in Odyssey history, that of Wooton/Penny.
Everything about Penny's character became a caricature -- where she was sensible before, no more. The plot basically took all the lines that Wooton might've had in some other episode and gave them to her. In short, she became a female Wooton. While being a female Wooton might not have been a bad thing, if Wooton was written as well as he was in, say,
Tuesdays with Wooton, or some other, earlier episode starring him, Wooton himself has been written poorly as of late, so the decision to basically clone him ruined both characters.
In short, it damaged Penny as a character just like how Mitch damaged Connie -- all of their worst traits were brought to the forefront, with no real development or substance.
Finally, the system was completed by the fact that whenever Connie had the chance to undergo character development, Wooton came along and ruined it by drowning her out. The original point of the arc was to develop Connie, but by effectively getting rid of Penny, that means that the only time Connie has a chance to develop as a character is when she's alone, and solo scenes don't work very well.
There might have been a point behind all of the chaos, but it wasn't shown very well in the story, so people mainly react to it by saying, "Great, another Wooton/Penny scene. How pointless."
So I could say that I like Penny, as she was originally written, but I don't like her after she meets Wooton.