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I've watched all three seasons more than a year ago. And I don't remember all details any more. So, my answers to your 4 questions will be more or less "I don't remember any more".
1. The story about connections between Mannings and Woody was abandoned. Perhaps if UPN wasn't purchased by CW, we would have gotten some new informations in Season 3 (?).
2. I don't think, that Beaver is adopted. He is Dick's biological brother.
3. We met Kendall as Dick Sr.'s trophy wife (she met all other 09ers through Casablancas family). But how was the beginning of her romance with Dick Sr. explained in latter seasons or if it was ever explained? Actually, I don't remember that.
4. Didn't Weevil just have problems with the law and needed a job? And when his cooperation with Keith didn't work, Veronica found him a job as Hearst's caretaker. But actually I don't remember details either. Maybe he truly didn't graduate (?).
Perhaps others will remember more.
As for Kendall and Duncan... it's a tricky question. Each time I watch that scenes, I see it differently. I should probably watch this episode again.
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