I finally got it working for me. MAKE SURE YOUR SIM IS CONNECTED TO WIFI Before you register. Here's how I did it.
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Click "Register Simulator" on the Playdate site.
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Click "Register". This should open up a Simulator instance.
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COPY THE ACCESS TOKEN, THEN PRESS "CANCEL".
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Go to the wifi section on the Sim, and connect via the test networks. (test1 is what I use, the passwords are the same as the network name, so the test1 password is test1.)
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Once you're connected, then in the Playdate ribbon menu of the window (just below the big border up top), select "Device Serial Number and Token".
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The access token area should now be blank. Paste the access token you copied earlier, and THEN, press Register and wait for the process to finish!
NOTE: The sim seems to forget the wifi info, so you will need to go into those settings and enter the password every time you launch it. At least on Windows, and at least for now.
I hope I helped someone. Also, my first post so, hi everyone!
-Nick.