Regarding the books: I'm going to be the odd one and say I actually stopped reading the books when I saw that they weren't going to have Chuck and Blair hook up, even as a one night stand. I saw possibilites and I thought it would be funny that if after Blair waited to lose her viginity to Nate she actually lost it to Chuck (oh how I love the show for granting me this).
I actually watched the pilot, saw that it was fairly similar to the book, thought "Oh well they aren't going to grant my wish" and didn't watch it until season 2. I only watched season 2 (and caught up with the rest of the series) because I was flipping through the TV guide (in Australia) and they were promoting the season 2 premiere by talking about where the couples left off and what will happen with them. I skimmed down saw Dan/Serena, Nate/Vanessa and then Chuck/Blair. I saw that read the bit about them and jumped on youtube to catch up, I was (quite embarrassingly so) excited about it then.
Wow, re-reading that I think its safe to say that I will never stop shipping Chair. Oh well.
About the Serena breezing through life and Blair working for everything. This is precisely why I like Blair more than Serena. Blair struggling to get what she wants is more relateable (also at times heartbreaking to watch) than Serena just being handing everything she wants and more.













