Yeah, "Boone became an alcoholic and died from it" except that I'm pretty sure I killed him early on in this playthrough.
Ahhh New Vegas bugs. I really hate how Bethesda screwed over Obsidian on this game, and how they tried to make it look like Obsidian was responsible for the bugs.
The stories that continue past the individual playthrough (the gist of what you mean, I think) is a fine idea, though I'm not really sure where I'd take it at the moment (something I'll think about). It would be easy for me to implement though, if you or anyone wants to make such content.
I thought about it, and I realized that what I really want are two things:
1. Minigames in epilogues. For example, visiting the Smiths after some (or all) of them have given birth to your sprogs, and having the option to refill their wombs with your kids.
2. Backgrounds/New Game + Mode that tracks what your character did before (in either the most recent playthrough, or based on a save file loaded) and changes based on that. So if the previous protagonist went on a rapespree in his playthrough, and then selected the new protagonist to be a product of his rape of, say, the thief, that changes things?
Hmm. Let me detail my second suggestion: A New Game+ that lets you save at the end of a playthrough, tracking the following things:
Goodsex/Rape/Mindcontrol/Murders Done
"Designated Mother" of next protagonist
Then when you load up that save for your New Game+, you can either pick a new perk/background, or go with your "parental perks".
Does this make sense?