I appreciate the idea for larger holders like him without younger generations to pass it off too, though myself I plan on passing it all to my children.

Saylor is a mixed bag. My opinion of him has changed negatively the more I observe his actions. I've always believed bitcoin's merging with the state is a natural step on the path to separation of money and state; leeches can't help but try to pull the life out of anything they get their fangs on after all. For all he's done for bitcoin adoption, his "end conclusion" seems to be that short-term outcome rather than the long-term solution needed...Whether it's unintentional, rooted in the here and now, or straight up nefariousness I can't bother to speculate too much on.

"Slay all of your heroes" was one of the best things I read early on into my journey with bitcoin.