Adding multiple files is currently available for student assignments in the LMS. Can this functionality be expanded to the Enrollment management system checklist steps?

Agreed. We need parents of candidates to upload multiple files for a checklist step. For example, we request multiples of things like report cards, standardized test scores, IEP/504, Therapy reports, etc. It is not intuitive for parents to combine everything in one file and/or many don't have the tech capabilities to do that. We really need this capability. Plus, combined PDF file would require a lot of extra work on our part to separate them, which we need.

I can see it being cumbersome for you break each potential item into a separate checklist step, as presumably not everyone would have each item.

But it still wouldn't work to break it down into individual checklist items, like "Current year report card" and "last year's report card"?

Since checklist items are pretty binary when it comes to whether the item is submitted or not, I imagine it would be more confusing to allow for "partial" submissions, where a parent could potentially only upload one of the multiple documents of the same type that you request.