First of all-I am a chronic overcooker for holidays. My holiday planning usually goes like this:
1) Plan a menu.
2) Decide something is missing and add 3 new items to the menu.
3) Go over it with DH. DH reminds me that 10 people don't need a turkey and a ham and 4 different vegetable options. Remove 4 or 5 items from the menu.
4) Look at it again and decide it just isn't enough food and add back 2 of the items previously removed.
5) Actual cooking and holiday meal.
6) Start telling people that they HAVE to take something home with them. DH and I (even with the cat's help) cannot eat all of the leftovers. Glare at sister when she says "Oh, I would have to leave you short." She knows better, but she thinks it is funny (every year) that I am such a bad overcooker.
So take anything I say with a grain of salt or three:
When I am doing desserts, I always make something that is traditional (usually pumpkin pie and pecan pie), something fruity (usually either an apple or a cherry pie) and something else (like a chocolate cream pie, lemon merinuge or a cheesecake or carrot cake). We invariably have more dessert than we need. But DH and my mom love pecan pie (and I am pretty fond of it). Sis's boyfriend and oldest child love pumpkin pie (and I like it too). My sister loves cherry pie and is very fond of apple. And I like to try something a little out of the ordinary for the holiday. We have, on occasion, ended up with a ratio of 1 dessert for every 2 people. Which is why people are not allowed out of my house at the holidays without taking some sort of leftovers with them. :>