I've seen that first image of Jim's bench a few times now.
I'll dare to make a few comments...
He doesn't have a megadigit bench DMM anywhere in sight and the items that look like DMMs seem to be stacked on top of power supplies (that act as a heat source).
So it does make you wonder why so many newbies on this forum seem to think they 'need' a super accurate/stable megadigit DMM. Maybe they are doing stuff that is at a higher level than Jim?
Also, I think a couple of low level shelves would have helped a lot. Also a deeper bench. I also suspect that the photo was taken at 'peak/critical mess' during a particularly busy time.
I am definitely a fan of ESD mats but this is mainly because a good one will act as a nice grippy and pliable surface to work on that is fairly tolerant of abuse from a soldering iron. I really like the old sky blue ones from Farnell. I suspect that these are now obsolete but they are really nice to work on and I also like the colour. Many years ago I used to just work on a wooden bench but because wood is relatively hard and smooth it's really easy for stuff to bounce and slide off the desk if mishandled.