Tsukuyomi is tricky because, like Kakashi said, there's no way to ensure that you're going to break out (bar some scenarios). If they assume that his genjutsu is like any normal genjutsu, they could fall for this trap and end up losing the battle because of that. I'd say that if the opponent is level-headed, has knowledge, and has a good counter to visual genjutsu, they may be able to escape it. Really it depends on the characteristics of their counter and how they use it, because all Itachi has to do is exploit an opening and they're done. I won't deny the counters you've posted though.
IMO I feel that Bee would fall victim to Tsukuyomi. There wouldn't be much point in Naruto warning Bee about it if that were the case (logically it should work too).