sageadvice
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So, Zabuza was 9 when he slaughtered the graduating class, and 26 when he died, back when Kakashi was also 26.
Zabuza slaughtered his class as a way of proving himself to Yagura, who had created a kill your classmate policy while being controlled by Tobi.
So, during that battle with Kakashi, Obito was either 26 or 29, depending on which source you use. At the time Zabuza killed his classmates, Kakashi was also 9, seeing as they were the same age. So, Obito was either 9 or 12.
Tobi was a full-grown man working with Yagura and Kisame. Obito was a squirt at that time.
So, it seems to me that we're back to the multiple Tobi theory, now that Obito is confirmed as Tobi, since he couldn't have been adult-sized while controlling Yagura all the way in Kirigakure while failing the Chunin exams as a squirt over in Konoha.
My thinking right now is that Madara was alive during Kakashi Gaiden and found Obito, and took him under his wing. When Madara died, Obito took the Tobi mantle from madara, like the next Dread Pirate Roberts.