What I do is call bellservices, they pick up the bags, I usually keep out bathingsuits, coverups, and ponchos or umbrellas(and put these items in a backpack or shoulder bag). I am not sure how bell services workes at POP, but I am sure you will handle it. Then what we do is take our bag on with us to what ever park we are going to spend the morning at(or the pool). If at a park, I check it into a locker. Then at about 1pm we head over to our new resort, to check in. If our room isn't ready we have lunch or go to the pool.
When we switch, we are usually told what time our bags will be there. If you have cold items besure to pack them seperatly and make bell services aware. I find it very easy...just a little planning for what you need during the day, since you might not have access to your bags for several hours.
As far as transportation goes, you go from POP to a park, then when leaving get on the OKW bus. If you want to do directly to OKW I would go to closest park or DTD and get on the OKW bus there. Hope this helps.