If I had to link two and two together I would venture to guess the grudge holding and the unrealistic expectations your H seems to have really do go hand in hand.
Your H creates in his mind how things should be no matter what (unreal expectations) and when his expectations are not met or they don't pan out he holds grudges.
You have mentioned twice now how he compares things to what his work friends have experienced. His work friends experienced difficult divorces riddled with financial terrorism. To him, that is how it will be. Never mind the details of the divorce(s) his friends had. His work friends can afford lavish trips, nice homes and have wives that make a good income. To him that is how it should be. Never mind the details of a special needs son or your joint decision to home school.
Your H seems to create an ideal life in his mind and then find others who have the ideal life he desires and when it doesn't pan out he gets pissed and holds grudges. He isn't interested in the details, he just wants the pretty big picture. You will never be able to change that about your H. It is his issue that he may or may not ever rectify.
It makes far more sense to me now why your H is so hung up on money and why he is so resentful about having to work so hard. He wanted his business to pan out in order to have the "picture perfect life" he created in his mind. He wasn't able to make that work and had to go back to being a "working Joe". He didn't like that. It was easier to blame you and your lack of income than look to himself and realize life *can* be "picture perfect" if you make goals. You said your H chooses not to make goals. He wants it all without doing any work. And when he does try to do the work and it doesn't pan out, well, he runs and stays angry and finds a way to blame somebody else.
IMO this is why it is crucial for you to focus 110% on you and building the life you need for you and your children. If your H does not address that particular issue your R will always have resentment, grudge holding, anger and comparisons between apples and oranges.
Your H reminds me of my H in a way. My H would put something in his mind about how things should go. Never mind he didn't actually do anything to make his idea happen. When things didn't go that way he shut down and ran. He has told me that is why he is glad his OW is so much younger. He has visions of molding her into what he things a partner in a R should be. While I realize there is nothing funny about this I do have to kind of chuckle when he tells me about all their problems. Everything he used to blame me for is happening with her. Since I am removed the common denominator is HIM.
