That's a nice stack Dan! Not easy to find so congrats.
I'm not so sure about the decal vs plate logo dates. I've got a few prewar tops and bottoms of different configurations. My earliest is a 2 drawer top chest that doesn't have drawer slides. The drawer just rides on L-shaped metal "shelves" that are tack welded to the interior of the box. It has a decal logo, I believe that it's the earliest of the Craftsman branded tool chests, first appearing in the 1939 tool flyer:
I believe Ooba Tuba has that 39 tool cart from that page, something that makes me eternally jealous.
Of the sources that I have available, the next time I see a tool chest is the 1940 Spring and Summer Big Book. Only sold as part of a set, the drawing has a stylized version of the oval decal. I've noticed the artists frequently took liberty to make sure whatever they were drawing displayed the Craftsman logo, regardless of what angle it was viewed from. Even so, the artist here was obviously drawing an oval decal logo:
The same tool flyer covers the years 1942 and 1943. This is the first time I see the rectangular plate logo. (Outlaw, are you sure your logo is brass? I've never seen a brass logo on a Craftsman box and if yours has one, it's certainly unique). This first clip is from the interior of the catalog, showing top chests with the rectangular, riveted on logo and drawer slides. Also note that the drawer pulls do not appear to be painted:

:
Now the back cover of that tool flyer. We have a rectangular plate logo on the top chest, an oval decal logo on the bottom chest. The bottom chest does not appear to have drawer slides. I believe this is an omission by the artist as I have an oval logo bottom chest and it has drawer slides. Dan, does your bottom chest (or the top chest for that matter), have drawer slides?
What I've noticed among the boxes of this era in my procession is that, in addition to the difference in logos and the drawer slide/no drawer slide issues, is that some have painted handles that are welded on and some have un-painted handles that are riveted on. I can't recall which is which logo-wise and I'm a bit far away from my shop to go look.
Another interesting difference is the partitioning of the main compartment in these two top chests. Not only are the trays completely different, the sectioning of the main compartment differs as well. Here is the oval logo 2d chest:
And the rectangular logo 2d chest. That tray handle isn't bent down, it's articulated at two pivot points, very different than the other box :
I suspect that there were 2 different OEMs for these boxes and what you got depended on the region you lived in. I can't prove that but my gut tells me that's the case. If we're talking which logo is older, I think existing evidence points to the oval decal being the older of the two.
Anyhow, great find Dan. That's a great looking set. Ooba....sell me that tool cart!!!!!!