Considering he, up front, confronted Kinkaku and Tobi and attached his shadow to them as they completely ignored him like his shadow wasn't there, he's not so smart. Because that's a pretty retarded move.
Remember in Part 1 where Shikamaru blindly was like "lol we need a sacrifice, ill go buy time gauize" and his master plan ended up almost getting him killed(he did plan on dying) until Asuma saved him. Gee too bad for a genius, he couldn't come up with a good enough plan to pay Asuma back by saving him...
Kiba is faster than Kisame, eh? Chiyo has better taijutsu than Orochimaru? Tenten is faster than Naruto? Hidan is stronger than Sakura? Because that makes sense.
I'd also take this moment to point out, if we are going by DB stats now, Tayuya had a 1 in strength and through brute force broke out of his shadows. Just saiyan. lolol
Regarding Kinkaku, He did succeed. Didn't you understand that he only needed to stop him for a moment for Ino? He just needed him to stay still for a second.
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As for tobi, Why was it stupid that he binded him using his shadow? he was saved by the gedo, he didn't ignore him. Just to refresh your memory, take a look at what tobi said.
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As for part 1, you do remember he was going against nine oto ninjas trained specifically for this battle. And he did succeed with his mission even though he had his chakra drained from his previous fight with Temari, right? I think he did the best thing possible in that situation. If you don't think so, then what do you think sasuke would've done? he would've been killed on the spot if it weren't for orochimaru's orders!