The design should work, but because the outlines of the pineapples are not one path, but grouped paths it’s going to be easier to snag a part of the image and shift a part of it.
SVGs should work as designed, but sometimes where there are lots of individual paths and many nodes, there is a greater chance of error coming in from the saving as an SVG and then importing into the Glowforge.
This might be what @rbtdanforth is referring to.
I wonder if this version might be better. Just trying it out. I joined paths and did a little cleanup.
Edit: fixed a couple nodes and tightened up the slots. Needs testing on cardboard.
The way I made the slots, you can edit the nodes easily to tighten them up to whatever thickness of material. Go into node edit and shift select the nodes of one side of the slot and then alt+arrow over, or however Illustrator does small nudges. Do the two exemplars and then duplicate and align as desired.