The quickest method would probably be to import the jpg and trace it using the pen tool. Simply add a small amount of code to the traced object to compute the area dynamically. Although your situation is highly particular, I believe it will serve your needs. I'm currently working on that screenshot.
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For individual support questions, you can also send an email. If you have a very short question or just want to say hello — I'm @olemoritz on Twitter.
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RE: Request for an App