SPC had circa 40s for this one, and the pair which were featured on the pipes revival blog with similar nomenclature were 40-50s.
American Estates Kaywoodie Handmade Carved Panel (circa-1940s) | Buy American Estates Tobacco Pipes at Smokingpipes.com
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Edit: I know nothing about kaywoodies. Just thought the pipe was interesting so started to look around. Good luck bro
There's a kaywoodie-centric board: kaywoodie - https://www.tapatalk.com/groups/kaywoodie/
50's and later was the 3 hole stinger, generally.
I figure all pipe are “handmade “.
Solved! Just as a footnote, a similar stinger and screw-in stem attachment was used in the regular factory run Drinkless series that was only discontinued a few years ago. I have a Ruff-Tone of that design, and the stinger is quick and easy to clean. The Drinkless series is still sold, but with push-bits. That's a fine looking pipe, clearly unsmoked in the photo.
The bit on my Drinkless was akimbo, but sable' told me to heat the shank with a hair dryer until the glue softened and set it right, which I easily did. It's a good smoker, and the finish has improved from a rather dull matte brown gray to a shinier stain with reddish undertones, just from smoking and handling it.