Hi Andrew and welcome to the forum!
Yes they can be tricky as they weren’t really designed with future dis-assembly in mind. I’ve uploaded a couple of pics of a Westclox pocket watch. The small cylinder sitting at the end of the brass pin (in pic) needs to be pulled up while pulling out on the crown/stem. I don’t really know the proper tool or procedure but I just reach down through the hole (second pic) with an old screwdriver and sort of leverage it up. I’m sure there’s a much better way though. Maybe shaping the end of an old screwdriver to fit the groove on the cylinder would help. Maybe someone up here can add more to this.
Hope this helps Andrew,