You may want to do two different loops...
MK and Epcot resorts.
Because the Wilderness lodge isn't on the monrail, you need to plan this as your first stop, or last..if the MK is open late and the boat transportation is running.
The WL and GF have awsome Christmas decorations. We did the monorail loop last year, just to get off and check things out. We drove to GF, had dinner and then did the loop before heading back to our resort. I will say that the contemporary was rather disappointing. A few small trees here and there, but their main tree is out doors..you can see it from the ferry boats that run between TTA and MK. Poly was nice, but didn't have that "wow" factor that WL and GF have. I know GF serves drinks in the lobby and you can sit and listen to the various music offerings they have throughout the holidays. Think I would start at WL...have drinks apps, take boat to MK. Get on resort monorail. It will take you to contemporary first, then poly then end at GF..where you could have dinner..1900 park fare, narcoosees, citricos or V&A....several different options. GF also offers afternoon tea that might be a nice starting point. Have a car would make things easier when moving between monorail resorts and WL and getting back to your resort when you were done.
Epcot -- There are lots of great dining options here ..all within walking distance around the lake. I don't remember if it was the swan or dolphin..but they have a not to be missed HUGE tree, the beach club has a nice lobby display and the Boardwalk is stunning. The chocolate and gingerbread displays are wonderful.
A great idea!! I'm sure you'll have LOADS of fun!! Bring lots of film!