We seem to do it each time now. It's so easy, and we love staying at a deluxe the first few nights - taking it easy, having pool days, etc. Then for park going days, we stay at Pop...no sense in spending $$$ on a room/resort that you are there only for sleep and shower!
It's SO easy. We pack one small suitcase to get us through the first few days. Then, on checkout day, we go checkout, DH takes a cab with our luggage to our new resort. The kids and I get on a bus to the park of the day. He checks us in/gets tickets, stores our luggage and then hops a bus there for the park. Last trip he was hopping a bus at CSR after cab/check in...at the same time the bus was picking me and the kids up at AKL. It's fast, convenient, and easy.
Cab ride was super cheap, too. You can let WDW do it all, but one of us would still need to get over to the new resort to check in/get tickets, so cab is easier...might as well bring luggage along!