As far as I can tell, buried under the last umpteen pages is the problem of making the "boring" mass-locked inbound bits less boring for the new player.
Yup. So I'm unburying it.
The idea was laid out by Admiral cim
It works, though, because while you're flying that distance the other ships in your patrol are chatting on the comms.
The problem with doing the same thing in Oolite, of course, is the scale - to get to Elite rank we're probably expecting the player to have built up several hundred (if not a few thousand) hours of flight time, so any comms chatter besides the professional (e.g. "target the Gecko", "requesting docking clearance", "your cargo or your life", etc.) basically needs to have a huge data source to work from so that it doesn't end up getting repetitive (something like CCL PhraseGen and similar can of course reduce the data needs, but not by a lot). The technical implementation would be relatively straightforward by comparison to the task of writing and collating all of that.
Similarly - and even harder in all aspects - with giving out mission hooks. Curse of the Black Sunspot was kind of an initial experiment in the direction of the sort of informal mission I think it would be excellent to stumble across (CotBS, because it's the only one, has to really give some heavy hints to the player as to where they should stumble about, and includes a lot more custom code) and choose what to do with. Similarly you might pick up a "routine" passenger somewhere, get dragged into the edges of something bigger when they turn out not to be who they claimed ... and it would be good to have "poke my nose in" and "get well clear of that sort of politics" both as valid options (and I don't mean "mission screen choices") with their own consequences. Somewhat difficult to code, but would need ridiculous amounts of background data .
 Well, to an extent. So long as it was being produced faster than the majority of players could consume it, it might be possible to do some sort of rolling release of that data file. That's still a big task, though.
Some replies included:
Could this be extended? Some brief commander biographies, stitched together out of a seed as per the planet descriptions? We've got a lot more memory to work with, so it might be possible to have rather more variety than the planet descriptions have.
Again, from a seed, there could be chunks of random news/gossip generated ... it doesn't have to be game-relevant, just mildly diverting (like the planet descriptions). And it could be occasionally game-relevant. People would get bored with it, I'm sure, but it really doesn't have to do much more than keep new players entertained for the first few trips - like your Freespace 2 example.
I don't know ... it's not just new players who find themselves stuck on a long journey in after a 6.4 jump wanting to save what little injector fuel they have left for actual combat. I think it needs to be varied enough that by the time you see a repeat (and even with generation it needs considerably more baseline data than the planet descriptions have) you've forgotten the original - something Random Ship Names, especially in the latest version, does very well. Otherwise I think it might end up breaking the atmosphere a bit for more experienced players.
Cabal Common Library Phrase Gen download
CCL Comms doc
CCL Phrase Gen doc
Comms Demo by Kaks original thread
Comms Demo thread 2
Communicating with other ships
Things to do when masslocked