When I add a stroke to a specific shape, the error: "Can't finish previewing. Cannot complete the requested operation." I am running macOS Catalina 10.15.7 wuth 40GB of RAM so shouldnt be issue of memory. Why could this be?
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Got a picture?
After I click "OK", it then goes in to outline mode.
Those are about a billion anchor points.
You need to simplify that artwork.
That's because its an image that I imported from Fresco to illustrator. Not sure how to avoid all of the anchor points. I could easily redraw, but I am trying to keep the feel for the vector drawing in fresco.
Try Object > Path > Simplify.
If you have Astute Graphics VectorScribe, try their Smart Eraser.