I can think of three reasons.
1. I think some people have difficulty seeing kid Obito and adult Obito as different people with different skills.
2. His motive for becoming evil turned him into a misguided figure who was easily manipulated by Madara. So his image as an intelligent guy has taken some damage.
3. He's gone through a character rewrite after his mask broke, so he suddenly doesn't think his actions through and he doesn't seem to analyse his opponents anymore.
Also, we still don't know why he has done the things he has done, like the Uchiha massacre or his attack on Konoha.
1. kid obito had good morals and values... life above the mission is what he chooses
2. *you let RIN die* is symbolism for people having to kill their friends, not being able to save people, breaking promises. He doesn't want things like that to happen anymore... he wants to make the world obey his ideals. Rin's death broke his heart.
3. When his mask broke, he was no longer hiding his identity. Kakashi knows who he is so now it is personal and Obito is showing it. He wants Kakashi to understand the way of the shinobi is wrong, and why you shouldn't give up on your friends and break promises. You should find another way out rather than the easy way.. Kakashi killed Rin instead of killing the Enemy ninja (he wasn't strong enuff too at that time) so he chose the village rules over her... (kinda like following in his fathers footsteps instead of killing himself ) in Obito's eyes.
Uchiha Massacre involving Obito prob included Danzo and/or gaining Sharingan power, eliminating potential threats to the Moon's Eye Plan *Infinite Tsukuyomi* since sharingan can break out of sharingan genjutsu.. other than make a deal with Itachi :ls:
