@alladojed just to add that I recently had a similar challenge in Google Sheets where I wanted a dropdown with multi-select capabilities (short summary: it’s not possible in GS without custom scripting, and all the examples I could find weren’t very flexible as they relied on hard-coded column references).
Anyway, the point of me replying here is that beyond the implementation of your custom dropdown in HoT is thinking about how you would deal with the display of multiple values in the cell after user selection in the dropdown. E.g. adding comma separators, or new lines etc to help with item delineation. Hope that makes sense.