Hello, Thomas,
On our next WDW trip we, too, have booked the Contemporary Resort, so it is a great treat to be able answer your question. However, I can only answer that being able to request an upgrade to a tower room upon check in is one of those things that could happen, but is never a certainty.
It does help that you are visiting during a quieter time, so that may increase the likelihood that the resort will not be filled to capacity. But, it is also a resort that often has convention crowds, so that could keep the capacity of the resort higher. You may want to start checking the WDW website regularly the month before your arrival to see what is still available at the Contemporary Resort by clicking on
Price Your Vacation on the
Walt Disney World homepage. You can also call Disney directly at 407-W-DISNEY prior to your arrival to see about the possibility of an upgrade and the cost involved with doing so.
And you know, sometimes upgrades just happen; it has happened to us a few times, and it is an amazing surprise! It isn't something you can rely upon or expect to happen; but if it does, it feels almost like winning the lottery.
Thank you for the question; please let us know if we can help again.