I think right from the beginning of the use of the word Boss by Ford, there have always been people, whether associated with Ford or not, that started to use "Boss" to describe anything exciting, or something with more power or cool factor.
In this case it might just have been an extension of that desire, more than anything actually related to any of the Boss engines being installed.
Regarding the timeline of drive-throughs, I was going to say at least back to the mid-fifties if not earlier (edit: Depending on the source info, it either started in 1928 or 1946). But widespread use was more a mid to late-sixties kind of thing.
That building looks an awful lot like a correct vintage late-sixties or early-seventies construct to me. No direct evidence, just a general feeling from the pic.
Similar to what would be cropping up all over the central and east states. I've seen that style building brand new as late as the late-eighties and early nineties. As said, brick along with that relatively basic building design is kind of timeless.
But it's hard to really tell as some architectural details even varied by region with regards to when they started. Just "looks" seventies.
Interesting that this truck is such a late '69 build. Still interested to know when the changeover to the side-marker lights occured. This one appears to have the electric wipers, the large front turn signals, but still has the reflectors.
Saw one outfitted just the same a few days ago. Got the VIN, but no decoding info on the build date.
Sure be interesting to hear any of the Marti info from the one in question in this thread though. Hopefully the owner won't mind sharing some of it sometime.
Paul