I'll be honest with you. Given the amount of complexity it would add to already enough complex Workshop module, I am not personally big fan of the idea. I do understand your use-case. Yet I think it is quite specific scenario, not applicable generally. The plan for future releases is to actually try and simplify the Workshop as much as possible (but not more than that). I am afraid this feature request does not fit much as a whole to the roadmap.
In any case, please feel encouraged to report and describe the feature request into the Moodle Tracker. Chances are that during the time, the idea collects enough supportive votes and evolves into something suitable and implementable for the wider users community.
Thanks for understanding.
Multiple Submission Boxes in Workshop
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