Wow, 7 holiday trips? Any advice for those of us who've never been in December? Favorite Christmas foods, etc.?
Get a parade spot early, much earlier then you think for a locals park. For the 6/6:30 parade time, especially on a weekend, people are on Main Street queuing by 3. It’s very much worth seeing it on Main Street.
The candy cane tradition is a cute thing to do and the candy canes are nice if that is your thing. The peppermint ice cream from Clarebelles/Gibson Girl is delicious.
The holiday cakes from Plaza Inn are lovely and very filling. If you are there for the Candlelight Processional weekend, try to go to DCA on the nights its on. Whilst it’s well organised, it can be a pain trying to get down/up Main Street.
If you get there at rope drop, you get on a lot rides quickly/walk on during the week. Even Peter Pan’s Floght etc we most locals don’t appear until mid morning/10:30 onwards I find.
For restaurants, we love Lamplight Lounge and Wine Country Trattoria. Carthay Circle is beautiful too (sorry, I haven’t scrolled up to see your travelling party/situation so not too sure what would be suitable for you/what you may like)
At Lamplight Lounge, even when they are closing, if you are sat at the bar/outside on the covered patio, they may ask if you would like to stay to watch WOC. Obviously it’s not a perfect view by any stretch but it’s a very cool POV if you’ve seen the show before. You aren’t allowed everytime, so not sure if it depends on your server etc.
The Holiday entertainment is just unmatched at DL (IMHO) don’t miss the Holiday Toy Drummers at DCA and watch as much of the storytellers as you can, check the guide for times. They are all wonderful and interactive. Nothing better than sitting with a drink watching a band etc.
Viva Navidad is wonderful too, great to see The Three Caballeros and the music/lighting/atmosphere is just amazing.
That’s all I can think of off the top of my head but please let me know if you have anything specific in mind too, want to see photos of something etc. The holidays at DL is my favorite subject
I’ve been to Tokyo too, please try and plan a trip there

Best parks in the world, DisneySea is like nothing you’ve ever seen.