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From UX perspective, a checkbox list will work better for all types of users. Because a user will be able to see some of the items immediately. It will force him to interact. The best practices are not to hide content under expanded controls.
[...] my goal was to eliminate the network shared structure. It'll help to center the goal around a clear pain point. You mentioned issues of 'g-drive' but the top two issues (length of the file path and storage space) are technical and not related to usability. From your description I think it's getting to the right information quickly that's the ...
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