That works if your cleaner will fold the shirts so they don't get (too) wrinkled in your suitcase. Otherwise you have to iron them anyway.

I may start doing that again, but I'm going to buy like 20 shirts so my personal schedule doesn't revolve around picking up and dropping off dry cleaning on my days off.

Always keep a pressed shirt in reserve in your closet... sucks to wake up at 0200 realizing that your alarm is going off in an hour and you forgot to pick up your dry cleaning. Also annoys the wife when you start washing shirts at 0200.