Definitely seen some of that Can DVD, mainly the live set. Have watched a documentary on them but I don't remember Damo meeting Malcolm so maybe I saw something different.
I basically thought "Hell Or Highwater" was okay but it was definitely less realistic than "No Country" (obviously not as good either), which is already kinda OTT. So the scenes with Bridges didn't bother me because I understood that they weren't really supposed to be taking place in the "real" world and Bridges was basically playing this version of himself he's been cultivating in his twilight years.
You picked my 2 least favorite cuts on "Grey & Pink" as highlights but you've remarked that you dig David Sinclair's keyboard sound so check out "If I Could Do It All Over Again, I'd Do It All Over You" if you haven't already- he sounds the best on that one, which is part of the reason it's my favorite.
Yeah, Stereolab are an atmospheric group that don't get much emotional involvement from me. Good music to have sex to. "Cobra" seems to be underrated (I prefer it to the *overrated* "Dots & Loops")- one of their better albums IMO.
You not hearing "More" until now is somewhat surprising but the fact that you're unfamiliar with "Cirrus Minor" and "The Nile Song" means you've also never heard "Relics" which is just nuts.