As usual, original letters can be found here.
LW#1: Your ex is kind of an a-hole, I will give you that, if your version of events is correct and, totally unprompted by the child, he just decided to take a dump on the fantasy that is Santa Claus.
On the other hand, by age 8, I think it's appropriate for kids to start discovering the boundary of fantasy. That is, at some point, they can't be thinking there are fairies and unicorns and Santa and his merry band of toy-making slaves, er, elves, and flying reindeer. But that's not all! There is the dark side of fantasy! Witches, evil powers, the devil, goblins and demons. Learning that those creatures don't exist, and that mankind basically creates its own hell with no supernatural prompting, is a lesson that is important, sad and at the same time reassuring one.
Think back on your own Santa revelation time. Mine was pathetically late, as I had "heard Santa's deer" on the roof during a period of skepticism/hypothesis testing one Christmas Eve and I was good until about 11 or 12, when finally I had to face the fact that elves did not make Fisher-Price toys, Fisher-Price did. Also, the time I didn't tell my parents I lost a molar and the Tooth Fairy didn't come and I threw a fit at the breakfast table, blubbing and declaring, "YOU LIED TO ME!!!" I was the sort who was not one to let the fantasy go, you know?
The point is, we all put this in context eventually. Usually within a few hours or days. Kids are actually quite resilient, and are better at taking in news than people give them credit for. What they really want to hear is that you will protect them, that they are safe, and that their trust is not completely misplaced. And I'm pretty sure that all of us who had loving parents were able to get over the blow, especially if our parents were sensitive about it and not caustic (like your ex) or mocking.
Also, I suggest that your last q: "What's there to live for when you don't believe in all the things that make a moment special?" Needs to be readjusted. I mean, you hear it all the time: Santa is not the be all and end all of Christmas. It's about family, love, religious faith, seeing light return to the world after a dark period, knowing that the worst is over. There are so many things that make every moment special, and the more your child knows about those things, and values those things over something make-believe and materialistic, the better off he'll be.
Best of luck!
LW#2: Everyone chips in $75 to buy the boss a present? What? Isn't he the one making the bank here?
Honey, I feel your pain. This sounds like a crazy situation. I suggest you find someone more experienced who you consider reasonable at the office and say, "Here is my problem: I live paycheck to paycheck and I can't pony up $75 for the boss. I'm not even ponying up $75 for my own mother. I don't want to be looked at poorly for this, but I am, in fact, kinda poor." I mean, first, get your arms around this thing and see if you're not reading overly-dramatic expectations into it. Because Jeebus, there is a recession on and I can't imagine the boss is really such a dingleberry that this is the kind of thing he expects at such a time, especially knowing his own workers' salaries. (OTOH, he has been accepting this, so that puts him in a messed-up light, too.)
Another recommendation I'll make for you is to read Elizabeth Warren's "All Your Worth." It is a book about budgeting that makes it *real* simple. And I'd tell you to start reading Michelle Singletary's comments on the Washington Post website. She is the "Color of Money" columnist, and although her philosophies are occasionally on the religious side, she has good advice in general. Because it sounds like you need some budgeting help in general.
LW#3: Give him a gift card from here out and he can use it to buy gifts for others. He's obviously got some kind of compulsion that you can't help at all. The only thing you can do is quit giving him meaningful gifts, because it turns his rejection of them into a rejection of you. So stop making your gifts to him about you, like the charity donations Prudie talked about.
Also, maybe you could ask him to research the best couples counselor in town, because obviously there is some chip in his brain he is bypassing and he could use someone professional (of his choice) to help him access it.
LW#4: Your mom sure sounds like some shrink. One wonders about the damage she may have inflicted on her non-straight patients. In fact, the whole drama of avoiding any personal questions to you basically undermines all her claims of competency.
But back to you. I think there is nothing wrong with spending the holidays with people who accept and love you for who you are, and I think there is nothing wrong about putting it this way to your family. It sounds like they are not ones for candor, but it is badly, badly needed in this circumstance.
That said, there is no reason to stir up drama about it. In fact, approach it as a logical conclusion of their rejection of you, say that you, too, wish your relationships could be closer, but you just can't get there because they don't want the truth from you, and until they accept who you are, they'll always be at arms length. Keep it brief, then step aside and let THEM make their own choices.
You are in one sucky position, but let's be honest — you didn't ask to be put there, and the people who did can undo it.
Best of luck.