In the case of Cliffhanger, I will definitly go for the DTS and anamorphic transfer over the old version I have.
Was Cliffhanger not anamorphic on DVD?
The only copy I have is an anamorphic LaserDisc. Unfortunately the transfer on that particular disc is nasty. The audio on it kicks ass though. I might actually pick up the SB release of Cliffhanger. Sure, it's cheesy & bad. But it's good cheese...

The original copy I have on dvd may be anamorphic, but it looks terrible... you can see the potential in parts of the movie for a decent picture.
There has been at least one re-master since the disc I have, but I am glad I waited for the SB version,
Cliffhanger = good cheese
A VS p = cheese gone bad.