Yeah, above posts pretty much cover it.
The soonest a conversation rewrite might actually happen (though it would likely not be the
final one) would be the personality rewrite, since those are probably connected facets. That's just a guess though.
Writing conversation simulators is hard, and currently there are only a handful of phrases conversation can use, which all follow a sort of madlib format. The only phrase structure currently understood by the game in a meaningful way is the name-phrase, which is "Word WordWord, the Word Word" (or something like that) and it doesn't even really understand that properly (exhibit A: every artifact name ever). With that in mind, maybe the first thing to happen will be better naming of things based on what they are and sphere alignments of things, but again that is probably a way off.
Toady has also mentioned that natural language processing isn't really something he's particularly interested in (as in, he'd rather program more realistic historical progression than try to make Siri), so there's potential that if some sort of convenient language processing library comes along in the next few years (which is completely possible) then DF might use that.
The main problem in my mind is that I doubt that it would be worthwhile to take a 5-year detour just so Toady could work out syntax generators that made sense
some of the time, because that's the sort of timescale it would take to get something really good together on his own, so my guess as to the far-future is that either an external library will get hooked in to do the job, or conversations will just kinda suck forever (though probably slightly less than right now).
To summarize:
-things to expect:
- more descriptive names
- more variety in phrase structure
-things to hope for:
- an externally-sourced language library gets created that DF can use
- personality rewrite affects conversation
-things to wish upon a star for:
- Toady to single-handedly write the best language simulator ever, and not take forever doing it
Again though - all this is guesses and opinion, so feel free to think this is all bollocks.