It all depends on when you are going in Jan. to DLR but as long as it's not too late in the month it should work.
Here's how:
You are going to get your first pix taken tomorrow on 11/24. Wait until the 30th day to upload them. That would be 12/24. To be safe if you can upload them on 12/23 that might be better. This will depend on when you get home on the 23rd or if you'll have a laptop at WDW while you are there. If you do you can access the disneyphotopass.com site (for FREE!) in your room. No $9.95 a day charges apply.
If you upload on 12/24 you'll have until 1/23 (30 more days) to order your CD (or 1/22 if you upload on 12/23). You can definitely get your WDW pix in and depending on when you are going to DLR you can get those in as well.
So when are you going to DLR in Jan.?
If you are going after 1/22 you can still do it-all you have to do is pay $4.95 for 7 more days or $9.95 for 15 more days. (a bargain if you can get all 3 on one order!).
Plus, you will need to have your last pictures taken in your account be taken at DLR in order to get the DLR price of $59.95. It doesn't matter when you upload them, the price is set by what pictures you have taken last.
You can buy the PhotoGallery CD while you are there this week ($59.95 plus tax, less AP discount if you or someone with you as an AP). Then just enter the coupon code in the promotional box when you order your CD in January and it will credit you the $59.95 and $2.95 shipping. A heck of a deal!
If you'll be going to DLR early in Jan. go ahead and upload the pix from this trip earlier if you can. The reason I say this is some of the borders may disappear. Though I'm assuming the Christmas ones are there already, and should be through at least part of Jan.
ADDED-Just checked the website and the Christmas ones for WDW and DLR are there. The 2010 borders are still there. (The 2011 ones usually show up a few weeks into 2011). Yeah-there are finally new holiday borders! I was getting tired of the old ones. Also there's a new DCA border whjich I like as well. The Halloween ones and the Thanksgiving one is still there.