Some of them are 19-21 years old. My sister flown on one of them couple of weeks ago and when I mentioned her before her flight that her jet is 20 years old..she was worried !! lol. She is not aviation freak like me so she doesn't know they are maintained etc...good looking birds but I guess time to retire. The one she flown is going to retire in 2014 for sure.
Possibly yes, with the exception of Japan (I think they're in a funny category in between regional and medium haul, as shown by what CX sends there).
The issue wouldn't be that, but more of a case of a non standard product. Australia, India and the Middle East are just about completely served with non-regional A333s (reverse herringbone Cirrus J product and new Y). The (re-)introduction of the 744 to these places wouldn't be a good look, seeing that there's a world of a difference between the two hard products. I don't understand why they would suddenly decide to keep them as they've accelerated the disposal of the 744 fleet and I also believe that the 77Ws are still replacing them on a rate of about one for one.