For Orthodox Jews holidays are a lot of work, and there are a lot of them! Except for Chanukah and Purim, we don't 'work' on the actual day, (driving, turning on lights or ovens, using phones, buying stuff) so all the shopping and most of the cooking (limited cooking can be done on holidays and none on Shabbat) has to be done before hand. So that is a big job. In the winter Shabbat starts at 4pm. Some people do 4 course meals every shabbat (which I think is nuts but people do). But def extra nice food. I make homemade challah every single week for example. Passover has a whole other level of craziness!
We just came out of a month of non stop holidays which were exhausting, Rosh hashana, yom kippur and then sukkot (2 days and than another 2 days) which mostly took place on monday and tuesdays so there was really no break!
I live in a different city to my parents and we can't get away for holidays due to work committments. Its pretty hard being away from family especially at Passover but its easier now my kids are bigger and real people. We always invite tons of guests over, especially lonely people who don't have who to celebrate with.
Chanukah is my fave though, no work restrictions, 8 days, and it can be as low key or fun as you want. Plus, latkes!
There is def drama in some Jewish families if the 2 sets of parents schedule the big chanukah party on the same night - obviously sat night or sunday are the popular times.
Some people just like to be difficult but it helps that we have so many holidays, Passover can be with one family, sukkot with the other.