You should do this:

just make the-
UT Server (id = 1)
Roger Wilco (id = 2)
WinAmp (id = 3)
UT (id = 4)

checkboxes, and use this if statement for On and off

Code:
; If checkbox is clicked and you unclick it, set the variable off
on *:dialog:isrun:sclick:*:{
  if ($did == 1) set %serveron $iif($did(1).state,off,on)
  if ($did == 2) set %rogeron $iif($did(2).state,off,on)
  if ($did == 3) set %winampon $iif($did(3).state,off,on)
  if ($did == 4) set %uton $iif($did(4).state,off,on)
}


that should work, havent tested it