This will be our first trip in 5+ years. Our first trip with kids and our first trip since the dining plan made ADRs a necessity. In the past when it was just DH and I we would book 1 or 2 nice meals and wing it for the others.
This trip we will be traveling in Jan or Feb (value) season. Due to the young age of our kids we eat our meals early (5:00-5:30 dinners). Will we have a hard time getting ADRs if I do not book them at the 90/180 day mark? We would like to do a few character meals (CM & CP but I think it is suppose to be closed)) and then the rest we would be pretty flexible.
This trip we will be traveling in Jan or Feb (value) season. Due to the young age of our kids we eat our meals early (5:00-5:30 dinners). Will we have a hard time getting ADRs if I do not book them at the 90/180 day mark? We would like to do a few character meals (CM & CP but I think it is suppose to be closed)) and then the rest we would be pretty flexible.

I would make ADRs asap for the character meals you want to go to. If you have a good idea of the TS meals for the entire trip, book them too. If you all change your mind on where to eat, you can make the new ADR and cancel the old one. I wouldn't want to take the chance of not being able to eat where I wanted and when I wanted. My motto: better safe than sorry or better to have a place to eat than not
It would not be fun trying to find a place to eat with hungry little kids 