If you were to put the characters as written into the modern day, around 20 years after the timeframe of the series, what do you think would stay the same? What would be different?
What it says on the tin. A couple examples from me: Drake could still keep his band and such, but could never get away with being a playboy for obvious reasons. He'd also thrive in a post YouTube world, assuming AI doesn't get involved.
Josh could probably stay mostly himself. Maybe he could post things about his passion for magic online. A theater job might not be viable nowadays, so he'd likely find something else to compete with Mindy over. Oprah could be debatable too considering how openly we know about celebrities compared to 20 years ago.
They'd easily have social media accounts that Megan would inevitably find a way to sabotage, but I'll leave what would be on them to your imagination.
Finally, I'd be impressed if there was a YouTube channel with just those cold open stories from the beginning of episodes.