Yes! I thought of that too. Cooper has effectively become what Phillip Jeffries was in FWWM, even down to some of the same lines ("We live inside a dream"). That's a huge parallel. Maybe his experiences in part 18 mirror what happened to Jeffries too (and likely Briggs too). Now when does Coop turn into a giant kettle?
I did notice that his face wasn't a still image. I kept expecting the main footage to cut to cooper and that it would sync up or something but it never did. it's showing cooper as being an observer of the scene as well as a participant. like he's watching the same show we are and his reflection is in the tv monitor. It's one of the strangest things in this whole series to me (which is saying a lot). Though yeah the time weirdness you mention is probably what it's actually supposed to represent. Also it's not the first time this happened! There was the scene where Laura's face was superimposed at the hotel room in one of the Gordon Cole and Albert scenes, perhaps that was done for the same purpose?
One thing I found really enjoyable about part 17, is that it's basically revealed that everything that happened was a part of Cooper's massive decades-spanning master-plan to defeat Bob. He knew exactly who was going to be where at what times and how to put the pieces in place from across time and space. That's cool as f*ck.
Also i've seen it pointed out that at various points in the series Cooper both has and doesn't have a pin on his lapel. and that could be a clue to piecing it together.
Mulholland Drive's "real world" in the last 30 minutes don't seem real at first because of how the scenes were presented out of order, but you can look at the continuity details to figure out what order the scenes actually took place in. So maybe cooper's pin is one of these continuity details that could help figure out the actual order of events.