Thanks. So I would engrave my raster, then scan/trace the bed and add a cut line? I haven’t used the trace function yet, didn’t know it would do that. Thanks!
Yeah, it’s pretty sweet! 
Got a tutorial for it here:
It’s going to be tough to come up with a magic outline method… it really depends on the image.
You can do an image trace with “ignore white” and stroke selected, and then play with the stroke width in image trace settings a bit.
You can use the GF trace tool (which I haven’t tried yet).
You can use Photoshop to create a path and bring the path into Illustrator.
You can get comfy with the pen tool.
You can get comfy with the pencil tool and smooth shape.
Lots of methods but I don’t know that any of them will be magic. Magic vector is another tool. The GF trace might be the quickest way to just an outline.
So much of it depends on what you’re trying to outline… the Photoshop way can be quick and easy.
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For basic shapes there are the rectangle, ellipse, polygon and star tools.
As others mentioned there’s no magic “make me a cutline” feature in Illustrator. If your raster is pretty solid you could run Live Trace on a copy (with ignore white on), expand it then Object/Path/Offset Path.
I’ve heard from sign makers that Corel and Silhouette Designer both have a feature that sounds like a magic “make me a cutline” but I don’t use either so cannot verify.
Macs and PCs abound at GFHQ, and we occasionally use Linux and Chromebook clients for printing too. Chrome is by far the best-supported browser on all platforms.
The only tiebreaker I know of is that I’ve heard Inkscape is significantly farther along on Windows than it is on Mac, so if you’re planning to use that, it’s a point to consider.
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