Originally Posted by
retiredfromhilton
For most people it's not worth the agony of booking say five one-night stays instead of one five night stay. But, as others have pointed out, it sometimes saves some money. (Other times it might cost some money.) . But another possible advantage to serial bookings is that, since free upgrades are contingent - among other things - on the upgraded room being available for your entire stay, you improve your odds for an upgrade with shorter stays. And, if you don't make yourself obnoxious in the process, the chance to discuss your unorthodox booking at check- allows you an easy way to request upgrades for any nights they are available.
It doesn't always work that way. We had put together 2 reservations for a stay at the Grand Wailea, and when we called to get a 3rd (I think a Citi free night had just been added to the account) they refused to book it for us because although a standard award room was available, it was a different room type than the others (2 beds vs a King). The agent said he was REQUIRED to book us into the same room type because we weren't allowed to move rooms during our stay.
Anyway, an award room that we could actually book became available, so we booked it and had a total of 3 reservations over a 5 or 6 night stay. Then we received an upgrade to Napua tower right before check-in, woohoo! But when we checked in, they canceled that upgrade because it wasn't available for the remaining nights on the different reservation.
All that to say, this is probably completely property dependent, but I wouldn't count on upgrades for some nights.