Hi Jaime!
Thank you for bringing your question to the Disney Parks Moms Panel!
The crowd levels for both weeks you mentioned should be pretty similar, with the January week being slightly less crowded. Those are both very mild weeks for crowds and would be a great time to visit.
Weather is unpredictable, but January should be cooler than November. Average temperatures in January reach a high of around 70 degrees, and in November it averages around 78 degrees. Those are definitely just averages and can trend much higher or lower.
The Free Dining offer has been offered in November before, but it's impossible to predict whether it will be again. Also, there are traditionally many blackout dates that may include the week after Thanksgiving for the offer.
If I had to choose a week, the week after Thanksgiving would win for me. Mostly because of all the unique holiday celebrations and decor. It's a beautiful time to visit Walt Disney World! I also love
Mickey's Very Merry Christmas Party that takes place at the Magic Kingdom.
I hope this helps! Please let me know if you have any other questions.