When the series relied more on B.S. than on character skill and logical thinking.
1. Picking a drunk, missing nin who is in MASSIVE DEBT, to be the next Hokage.
2. Sasori losing to Chiyo (and Sakura, I guess). I didn't think Sakura was good enough to be of ANY assistance in that fight (if you look at her skill set back then). Then, of course, he suddenly decided that he needed to kill himself right when he was about to kill them both (because that made SO much sense).
3. When Hidan suddenly "cursed" Shikamaru during their second "fight". Last I checked the Jashin ritual required the user to be inside a Jashin Circle for it to work. Maybe it was just me, but I didn't see a Circle. Did anyone else?
4. Kakuzu, the 70+ year shinobi veteran, getting caught by a Shadow Clone of a Genin (main character or not) and getting hit by w WIND attack that he identified (as a wind attack and dangerous one) before that. Call me crazy, but I believe he had the Fire and Wind hearts and was spamming them to kill the rest of the enemies.....why didn't he just use it on that attack? (Because then Naruto wouldn't have been able to show off his cool, new jutsu!!)
5. Sakura pulling the White Seal out of her ass.
There are others, but those are my main ones. Truth be told, I've considered the series itself to be just one massive disappointment for a while now, so I guess that's number 6.