The issue with restarting the generator is that you might not want the world to advance by more than a decade every time you play (especially if your characters tend to die immediately), but it would be cool as an option, and it would give you the opportunity to have more impact -- however, most of the impact should be during regular play instead of through a Q&A process, I think, so maybe it's not much different from the retconning approach in retrospect. With retconnning, you'd still be able to make decisions -- they'd just only be able to seriously affect the other new characters that have been pulled up from your abstract population. That isn't all that bad, since the populations can have attached historical events, so it can be very thorough with respect to the existing history, and you could meet the real old historical figures, just not have an effect up to the level of, say, killing them or taking their important things. It could insert new events back into the old histories though. You'd just not want those to make subsequent decisions seem odd.
An exception to the lack of impact (either desired impact in the restart-generator setup or technically feasible impact in the retcon setup) might be the start scenario, as it could involve some of the main historical figures sacrificing you by dropping you into a cave or something, but that is essentially a restart-generator scenario that has run a very short period of time.
Yeah, starting the generator at birth would be a drag if you wanted the ability to quickly follow up on events that happened in history or fortress mode (or happened to another adventurer). You can run history for an arbitrary period
after retcon... I don't think you'd generally want to retcon a player character after generating its history, though.
I can envision a reasonably graceful way of letting the player choose how much retcon and how much history generation they want, without flat-out telling them "this way is fake, this way is real." Say on the character creation screen, the game asks for your current age (X), which you can set from 0 to some reasonably high value. The game then retcons X years of your life, does the Q&A thing as appropriate, presents you with the results, and gives you the option of a) starting now (possibly disabled depending on circumstances, since we all know babies aren't sentient) or b) nudging history forward another year, which will do further Q&A. So you could roll up a 30-year-old adventurer with no lapse in game time, or wait 16 years to grow up seamlessly interwoven with the game world.
That raises the question, though, of what part of the game world they should
be in. Starting in a city is easy since they're big abstract populations, but I think it's important that the player also be able to insert themselves (as a newborn or whatever) into specific ongoing stories as circumstances allow. For example, it would be cool to be part of a refugee group from your last fortress, but plopping you down as a newborn would have issues -- there'd have to be the appropriate romances, the player could be forced into certain roles as Heph mentioned (although many players would enjoy that), etc. Retcon probably wouldn't work at all, unless it was explained as a newcomer encountering the refugees in the wilderness, which might or might not be reasonable depending on the group's isolation etc. Yeah, there's a lot to tackle there.
Toady how are you planning the conservations between Player and Person from the DF World? Will it stay the way it is right now or does the player get a more active way to interact say with a Dwarf like with a nother player in a pen & paper game (as the other end of the extreme)?
I dont ask for an entire chatbot, which would be anyway more then awesome with all that personality stuff, but it would be cool to do some everyday chatter without getting "Its nice weather" from every second peasant or asking a farmer if he did see the monster that terrors the place. (That begs for another question: is the time on hold while i talk with someone?)
Some kind of input field could be neat where i can insert maybe a "Name" or a "Keyword" and the Peasent to which i speak gives me his oppinion on this person/theme as long he knows something about said person/theme.
There's a lot of dev notes stuff that tangentially imply major changes to conversations, but this one mostly closely addresses your idea:
Bloat201, CONVERSATION UTTERANCE BUILDERS, (Future): When asking specific questions or making statements, much like wrestling, you could set specific parameters. You could set a topic and a question word or your topic and intention and a tone.