So, I did manage to figure it out and make it work, but it’s sub-optimal:
as @md8n pointed out, this was the big “ah hah” moment for me as I re-read this post (yay rubberducky debugging), I noticed that the paths were all positive numbers.
So I went in and manually set the depths for the drill and perimeter… and the drilling still didn’t work quite right.
The issue was probably linked to @ame and @Orob’s points about incompatibility that was accidentally fixed by the forum post I found on the freecad forums, but I can’t find the link for.
It pointed out that adding the additional parameter:
--translate_drill
Changes the G83 and other less generally compatible grbl gcode to more “normal” z-step gcode.
So I managed to drill and cut out a cribbage board
But now I’m curious how to setup FreeCad to be happy with, and properly simulate, negative cut depths, and what “Work Coordinate System” I should be choosing, if any?
G54, G55, G56, G57, G58, G59, G59.1, G59.2, G59.3, G59.4, G59.5, G59.6, G59.7, G59.8, G59.9
It feels so fantastic to be able to get something working who, even if it’s a manual pain in the butt right now. Got the board on my bench. 
Thanks for the help so far everyone!
OH, PS: For drilling into plywood, pecking doesn’t seem to be necessary, at least for depths near 5mm. And using pecking makes it So Slow, OMG.