It's luck! that is the only way to get one....the right place at the right time. We have gotten free upgrades several times now. Over the past 5 years we have been upgraded at WL, AKL, BC, BWI and stayed at CR several times and never upgraded there. It depends on crowd level....going during a holiday means the resorts are full and the CMs have no flexibility. Arriving late or early doesn't seem to matter because we always arrive early. Stayed at value resorts about 25 times and only upgrade once there (upgraded to another resort CSR). Stayed at moderate resorts about 15 times and only upgraded once or twice there (water view room). We seem to do our best in the delux resorts because there are more options. We never expect it and it's always a surprise to us. We are prefectly happy in whatever room we reserve. We are now DVC members and upgrades there are unheard of and that's OK with us. We do stay at the resorts in addition to our DVC stays, but not as often now. Usually a day or two before moving.