First one, I'd rather translated it as "Everything...has gone just the way I like it." though.
Second one, personally I think your one seems fine, though if it's me, I'd rather put it as "W-...Well, I bet he should be able to manage that hmself" though. Not the best way to put it,though, so maybe you should also look at what others have to say on this.
Third one, "nna" = "anna". So the actual sentence would be "anna koto itterareru ka". That should help, I guess.