From an end user point of view, I have trouble understanding what's happening in the menus also.
Are server side cvars that difficult? There's a create cvar command, correct?
No extra file is needed to store the actual settings, right? Aren't they stored in some Gmod server file by default?
I've done no Derma or Vgui coding at all. (Umotd is 100% ripped from Megiddo's original motd client code)
I admit, I could be just smoking something since I've not ever dug into it.
I'd share if I could.
I think Checkboxes would be easier for some of those functions you now have menu popups for.
Perhaps looking into UPS options area would give some insight to how to do them.
(I know it's where I'd start.
)