BC,
In general the hotel is busy on most weekends throughout the year. Even during the off season.
Since the first 2 nights of your stay are on a Friday and Saturday night, the hotel has a big chance of being sold out.
If they deny you an upgrade at checkin and you are willing to change rooms, I would ask if they can upgrade you for Sunday, Monday, and Tuesday nights.
Of course conventions, groups, or the hotel being sold out could put a damper on your upgrade chances the entire stay.
-Jon