I've seen a fair few WSOp (Cmn) return to OASC, be selected for pilot (and other branches) then commission and complete their training. However, I have seen a greater amount go to OASC and fail and then stay where they are without even wanting it.
Just so you know, funky, the training to become a breveted WSOp (rotary Cmn) will be 2 years minimum, with at least 6 months in an ocu. You'll then have to complete a frontline tour (at least 3 yrs), probably 2 (6), before your chain of command even consider letting you move on.
My moral is, only become a WSOp if you want to be a WSOp, don't use it as a vehicle to transport you to greater things, you'll only be disappointed.