If I were you, I’d avoid adding modifiers to the Winkey combinations. It doesn’t work as easily as any other +^! combination, because it’s a special case.
You can add sleeps and sends as you wish to modify a hotkey. For example, if you have assigned the Play button to edit the info line, you can use v to send the other command.
You can also do pairs under circumstances. e.g.
v & 1:: do one thing
v & 2:: do another thing
v & 3:: do yet another thing
but v will not do anything on its own.
Generally, I assign things to ahk so that they are invisible to Cubase, OR make them work only #IfWinActive, so that I don’t mess with Cubase’s assignments.