tldr; Best way to create perforation outlines for stickers (text, vectors, and PNGs)
Hey everyone!
I'm working on a sticker project and could really use your input.
Goal:
I want to create stickers on sticker paper and export perforation paths for cutting machines like Cricut or Silhouette Cameo.
Until now, just adding a thick stroke around my design worked fine.

The Problem:
Now I want to generate a cut line — like an outline around the design — to be used as a perforation path.
I’ve been manually doing this with the Pen Tool, like this (screenshot attached) — just a cloudy box shape that wraps around the sticker.

But:
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It’s slow
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It’s hard to get clean, consistent results
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And aligning everything properly (especially with padding) is tricky
I’m aiming for something like the attached example: smooth curves, sharp corners where needed, and even padding around the content.

❓Questions
Q1:
Is there a smarter or faster way to do this than using the Pen Tool manually?
Especially when dealing with multiline text?
Q2:
Would your method also work if I want to wrap a group of vector elements (e.g., icons, decorations, etc.)?

Q3:
For PNG images, I use a plugin called Quick Tracing to turn them into vectors.
Is there a way to extract just the outermost shape from the traced result?
Or any other method to cleanly get an outline for cutting something like a Tom & Jerry image?

I’d really appreciate your help or ideas. If you’ve run into this before or have a better workflow, I’d love to hear it.
Thanks in advance!