MSYtoJFKagain

Hi everyone. I've been asking bits and pieces of advice on various threads and figured I'd start a post to keep things contained.

I'm going on my honeymoon next February. (1st through 21st ideally)

I've made a lot of headway on planning our travel but I'd love some input. I'll post the current details below.

Depart JFK to HND - F Rewards on JAL
7 days in Tokyo, 2 of which are at Tokyo Disney. Staying at Hilton Tokyo (JR pass activated 2nd day of Disney as I won't be going to the park but having a solo day trip to Hakone)
5 days in Kyoto/Osaka/Kobe, staying at the Osaka Conrad.
1 day of travel up to Hakodate, staying at the Four Points Sheraton Hakodate
1 day in Noboribetsu at Takinoya
4 days in Hokkiado, staying at Comfort Hotel Sapporo Susukino, 1 day trip to Otaru in there somewhere
3 days in Tokyo, Choice hotel redemption nights at best available Tokyo hotel
Depart HND to JFK - F Rewards on JAL

I'm struggling with a few things.

We'd REALLY like to see the snow light festival in Otaru and the snow festival in Hokkaido but I can't seem to find out when they actually are.
I've got a giant pile of restaurants and activities for every city but I'm not sure what would be doable in the winter months. Examples would be: Maker classes: Miso, soy sauce, knives, along with tours of those kind of places. Cooking classes for ramen, kaiseki, etc.
I'm also speculating whether it would be better to break up those last 3 days in Tokyo to extra days elsewhere? I'm placeholdering them right now in case we need to push things backwards and forwards due to reward availability.
Also, is Valentine's Day a big thing in Japan? My SO and I hate it because we've had horrible luck every year we've tried to do anything but sit on the couch and relax.'

Anyway, thanks for reading my TED Talk. All advice is welcome.