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did you ever figure it out, im curious too
AddonName>materials
AddonName>models
AddonName>maps
-etc
With AddonName being the addon base folder with all it's contents inside and is what you select for content folder during uploading. I did not try using vpk so I don't know if that works. If not, you might have to extract it into the base addon folder.
I had an issue where I used an icon image 1600x1600 that caused it to fail, however I exported it as an 600x600 png and it worked. If your upload fails it will create a blank workshop page on your profile that you will have to delete.
Once uploaded you can change the description and images for your mod. If you are reuploading an existing mod from a site like gamebanana, I would recommend contacting them first as they have the right to remove reuploads of their works.