Nick's problem with women is likely from a couple of angles from his childhood, but likely not from the money dynamic.
- Dad wasn't home for several years, as he was working at Cray in Minnesota and commuting back once a month to Houston. Mom was the de facto head of house for some time until they moved north. (This is why he wouldn't shut up about the lost Starscream, it was a gift from Dad for being gone.)
- Nick has an older (half?) sister, who apparently dressed Nick up as a girl at least once. She may have been the dominant force in his young life.
- The trust likely wasn't a factor in this. Celeste's Mom and Dad didn't get the stock rewards until Nick was older. They were still doing well, but not "we'll add a wing to the hospital" well. Even then, grandpa was the one who earned the stock. I don't know who's running the existing Trust. (For all we know, it could be Ty Beard.) Mom maybe still ran the purse strings in the house, given that dad was gone in the early years, but it wasn't while sitting on a Scrooge McDuck pile of money.
I think that more than the female angle, Nick shares a lot of his issues with lowtax. There was a certain malaise for late gen xers and early millennials, you could see it in the music in America. It was cool not to care.
Beyond the zeitgeist, both Nick and Rich never really had to own up to their own actions. Mommy and or Daddy was always there to make things better. Hell, they both managed to fail upwards in spite of themselves. Lowtax's ultimate enemies, in his mind, were the shitty forum users who would dare go against him, as well as his wife and ex-wife. Nick probably hates Kayla at some level but can't admit it. But like lowtax, he hates his former pay pigs. Instead of a wife to (openly) hate, he hates the farms as his jilted lover.
(Many other parallels- pedos for friends, their response to adversity ("muh kids"), their response to success, their falling into drugs...)
I know Nick has NPD and thus is unlikely to self delete, but I still see that as the most likely outcome for him, because it's the easy way out. You know, if you can get his guns back, and when the money runs out.
Edit: clarity and grammar