[i]Mm, so in general, it's still expected that everyone's characters are on the same time and will be partying together (so whatever social/occupational obligations they have will take somewhat of a backseat)?[/i]
No. I intend to tailor their environment to whatever situation they find themselves in. If they're partying together, we'll have a party-centric story; if they split off to take on other obligations, we'll tell those stories instead.

[i]Also, noticed a bit of a discrepancy between when everyone's popped into the new world. I'm guessing that's just a side effect of everyone having different methods of getting isekai'd?[/i]
Pretty much.