You would definitely be waitlisted. We waitlisted last year about this time for a two bedroom and a studio for Dec 28 to Jan 6th and got them both eventually. They have changed the waitlisting procedures a from last year. I waitlist for everything that would work for us on a day by day basis, if the day became available I took it and removed the wailist on the other categories so we would not be changing rooms. I believe you now need to waitlist for all the days you are looking for, which makes it easier to monitor but means if 7 or 8 days become available you would not get the 7 days even if you could make it work. I think you toughest night will be New Years eve. You might be able to waitlist as a split stay the first x days in one and the remainder in another. This way you increase the chance you get part of your stay with
DVC points. If you are flexible on the resort and the room type you will increase your chances.
You would need to buy through Disney, these points can be used, waitlisted, almost immediately if you let your guide know. Resales can take two months to close and get in the system available for use.
If you consider the closing costs and points available often Disney is no more expensive than resale and it is much faster and simpler. (If you purchase a use year that starts after your purchase date you get the points for the previous year, 2007, which you can bank; the current years, 2008, on your use year and you pay maintenance fees effective the date you purchase. (So on a 200 pt contract with a Sept UY purchased Aug 1st you would get 200 2007 pts August 1st which can be banked, 200 2008 points Sept 1st and you will pay 5/12 of the 2008 maintenance.)
Also remember the discounts. If you do not already have an annual pass and are planning on getting one you can save 100+ per person.
Good luck.