cave generation/time lapse

[gnarlytreeman]

so i haven't really spent much time caving. 1 because of previous molestation while there, and also because there is no free pop back to the surface and stay alive thing anymore. and lastly because i have to work for a living, and only now have some free time.

 

so what  i was wondering is if i'm playing on an older world, does the world gen in the caves continue from the first time i enter a cave, or from the begging of the game.

 

2ndly why doesn't my stuff stay in chester traveling to or from a cave? i thought that would have been fixed along with the day counter, it makes no sense to have him and him not be useful to tote junk in between.