Ouran High School Host Club is pretty funny and most people in the "anime watchers out there?" thread will agree. It's a reverse harem and shoujo anime with the ending mildly being dissapointing. Mainly because you'll want more. Angel beats' also pretty funny.
What genre do you like? Sword fight, mecha, fighting, romance, comedy etc.
My top 3 favorites that would recommend is:
Yu Yu Hakusho - Fighting
gurren lagann - Mecha
kuroko basketball - basketball
Others i highly recommend:
Samurai Champloo - Sword fighting (on netflix)
Attack on titan - Action & Gore
Trigun - Post apocalyptic gun fight (on netflix)
Deadman Wonderland - action, fighting, powers, prison
Comedy is hard for me to recommend because it all depends on what you find funny
Yes, I'm currently about half way through book 5. It took me around a month and half, maybe 2 to finish each book, but I took a big break between 4 and 5.
Season 3 is roughly half of book 3, with the season climaxing with one of the series biggest spoilers which comes up about halfway through Storm of Swords. once you hit the big moment (you'll know what it is when you read it) it is safe to start watching the season.