I have done a split stay on my past two trips. The first time (December 2012), we stayed at Pop Century first and moved to Port Orleans Riverside for the rest of the trip. This was a bit of a hassle because we had free dining with the Riverside reservation, so we actually had to check in before going to the parks that day to have access to our dining plan. So, we had to take a bus from Pop to Hollywood Studios and then grab a bus to POR. Other than that, no real complaints. We took all of our luggage to Luggage Services at Pop that morning and they transported everything to POR for us.
When we did it this past week, we stayed at All Star Movies first and then transferred to Art of Animation. Easy breezy lemon squeezy! No meal plan or anything and they don't close out your account until midnight the day you check out, so we dropped our luggage off at Luggage Services at ASMo that morning, headed to the park (Magic Kingdom, if you are wondering), and at the end of the day headed to AoA and checked in. Now, they wouldn't put our luggage in our room until we actually checked in, so we did end up waiting about an hour for our luggage, but we ordered pizza, watched a movie, and didn't really notice.
My husband and I are on a mission to stay at all of the Disney resorts and since we aren't the most patient of people, split stays work well for us. That way, we can determine which hotels we love and which ones we would rather not stay at again. Oh, and there has only been one resort that has ever fallen into the latter category.
