FWIW - we did this EXACT scenario once... ONCE. Never again. We ended up having to cart our own bags (6 of them - because my kids were too small to help) about a half mile through the resort to our next room. We did "connect" them...but our 1bedroom was clear on the opposite side of resort. We could have left our bags for bell services, but didn't want to... we were too afraid they wouldn't transfer properly. We were basically out of commission for an entire day, between packing, bag transfer, walking, packing "extra" bags with immediate needs while we were homeless, and waiting/texting for new check-ins. Then unpacking...again. It was not very "vacation-y"... and I don't think we'd do it again.
Someone on the dis gave me good advice once... you bought points to use them and enjoy them. Don't skimp on the points if it will negatively effect your vacation. You bought them..... use them

My 2 cents.