There is really no way to know what your chances will be. It will depend on how many people are ahead of you on the waitlist and how many reservations are canceled between now and then. January is a prime time for DVCers to visit WDW as the points-per-night are the lowest of any season. Do you have a back-up reservation somewhere just in case your waitlist doesn't come through?
As for the pool view, only you know what you will be happy with. Pool view rooms have a view of, obviously, the pool so if that's fine with you then you'll be all set. We have stayed in Boardwalk View and Standard View rooms at the BWV and have enjoyed both.