Struggling to get My Tags edits to reflect on USB and in Rekordbox search

- Latest version of Rekordbox

- MacBook Pro 15" w/ latest OS

- XDJ RX2 w/ latest firmware updated

I originally made a tagging system that I hoped would work on any gear I jump on.

I used My Tags in Rekordbox to create shorthand such as "[dh" "[sx" etc.

I was pumped how it worked within Rekordbox as I essentially could whip up a playlist in any given moment based on various parameters and descriptions of songs.

However, the huge bummer is that the symbol "[" isn't searchable on CDJs or XDJs :( So I instead edited all My Tags to instead start with "#" as in now "#dh" "#sx" etc.

However, not only do the My Tags not show up as edited with the new symbol "#" on the song files' info under the newly transferred to USB in finder (which maybe explains why I can't search them on the XDJ RX2), but I can't even search via My Tags in Rekordbox like I previously used to with just the search bar ...

Am I missing an extra step that finalizes the My Tags edits? I've spent so much time searching/reading and I don't get how to fully get those to switch to the new edits.

Thanks to anyone who can help me get this figured out or even just a lead.
Cheers,