1. No
2. No
1. Probably not
2. Yes, of course, he shouldn't be the one asking for forgiveness.
Food for thought.
Itachi killed the Uchiha because he was told that the civil war would bring an end to Konoha. The reasoning was that Konoha would be invaded by the other villages because of its weakened state.
Pain destroyed Konoha and killed the majority of its citizens. Orochimaru invaded Konoha and as well and plunged the village into turmoil.
How come it wasn't invaded by any of the other villages?
To me, it sounds like the Uchiha massacre was all for naught.
I get your point and it could be like that, but imho, Itachi did the right thing for his age.
But like he said when he died, maybe he should've told Sasuke about it and kept a closer eye on Shisui.