1. The whatever sharingan requires nothing more than for their eyes to meet. Aizen has no idea whats coming. Once in his Sharingan Aizen is pretty much a dead man or close enough to it. He has no reason to avert his gaze or anything like that.
Also Itachi doesn't need to do any hand signals to use other Genjuitsus he only needs to point a finger at Aizen. Hell his shadow clones can cast genjuitsus for him.
2. This seems to be based on the belief that Aizen is faster than Itachi. Or can move faster than Itachi can react and this is pretty much not true. Saskue was able to percive someone moving at the speed of light with just one level of his sharingan as his sharingan moved up he was able to perceive faster opponents. While I don't belive that everyone in the NAruto universe is flying around a t the speed of light they sill move extremely fast and there is no reason to belive that Bleach characters are faster. Unless you have some sort of objective measure of their realaitves speeds so that we cna say X is definetly faster thant Y. Cause right now there is no way to know for sure that Aizen is any faster than Itachi.
Also as for destrucitve power Akatsuki members are turning miles and miles of ground into charred craters in single attacks and several could level a city if they tried hard enough. Hell Kisame who is weaker than Itachi turned a Desert into a lake. So don't try to tell me that Bleach characters are more powerful.
Another thing is that ITachi is probably mostly blind and Aizen's illusions might not even work since he can't see it. Evne if they did Naruto characters have the ability to dispel illusions with Techniques as aoopposed to Bleach characters that don't seem to have any effective ways of actually dealing with them.
So it pretty much goes like I said. The two look ata each other and Aizen is done unless he has some sort of knowledge about the Sharingan but the OP didn't state that.
this is a LITTLE hard to call. neither characters have truly shown their strength. however from the looks of it. naruto characters have currently far surpassed the power levels of bleach characters.
itachi>>>urochimaru>>>>>>>diedara who created a pure blasts wider than 20 kilometres and higher than 100 kilometres with his ultimate jutsu. theyr starting to make nuke level attacks look like childsplay.
another thing about the speed. naruto characters with body flicker have instantaneously moved from country to country plus haku's lightspeed etc. their is ZERO evidence to support that bleach speed>naruto speed.
aizen is at a disatvantage because he creates hallucinations which can be countered by not having one of the senses. plus the shaaringan is a sure bet illusion KILLER. not to mention the nuymerous powers it has far surpass sousake's shikai. tsukiyomi iis a far stronger illusion than sousake's shikai. not to mention amaterasu{and his true skill has not yet been revealed} will kill him. aizen also can not cast off itachi's genjutsu.
im still waiting on aizen's bankai and arrancnar/hollow powers to come through. but currently, aizen loses big time.
1. Your logic is flawed my friend, just because Deidara can make a blast that large does not make that feat(which also killed Deidara I might add) Itachi's.
2. Instantly moved from country to country? Bullshit. Haku's lightspeed? Are you saying that Sasuke's fireballs are lightspeed as well, because Sasuke caught him with one, and you could see Naruto moving when Haku was, and Naruto can't even move faster than sight.
3. Aizen's illusions cannot be countered by Sharingan cause they use no chakra.
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2. As for the instantly from country to country thing I am not aware of that. BUt as far as haku's speed. They said that in the anime I think the english dub but Ii m not sure. While I don't belive its true I do belive he was moving at incredible speeds. The point is that the speeds in Bleach are nothign special at all.
3. We don't really know how chakra and spirit energy are going to mix if the two fight fora l we know none of their illusions will work and they will have to hand to hand it.