We had 4 rooms, asked for 2 of the rooms to be connected (a specific 2, yes all info. on 5he request that was faxed and given over the phone was correct) and to be on ground floor of possible. We got there and those 2 rooms weren't connected and we were on 3rd floor. At first we thought that it just wasn't available (odd as we've always gotten connected rooms when asked though), we start to leave the checkin desk and I pull up a map of the resort rooms on my phone and find out that in our group of 4, 2 of our rooms are connecting just not the ones we asked for. We all got there at the same time etc., we went back to switch the rooms around and my mom (has some mobility issues and cant do stairs) mentioned that she was also hoping for ground floor. The CM who was helping us was great said he'd look and very quickly found 4 rooms together (2 connecting) on the ground floor and moved us there. He told us that it really just depends on the room assigner and that some are better than others at looking for room requests, so I will always from now on ask at checkin if it's something I want instead of just assuming they must not have had it available as there's no way that neither of our last requests weren't available, especially the connecting rooms one, it was, it was clear which rooms we wanted connected, they just didnt care or look etc.
ETA: Yes, the rooms were in the same preferred category and even in the same building.