And for some, seeing a constant popup will be annoying.

I know it will for me if it isn't with people i know.

And it's always fun when I run into people in the next roulette two - three times consecutively.

In the end, what you're asking for is a Drop me into the Roulette Gauntlet with the same four ppl. and then the last few will be all content that requires 8 ppl. (But roulettes are meant to help people in need of players for content. removing the purpose and the reason they get paid for running it. Thus it'll only be for 2-3 Players and them 4-6 for 8-man content)

But doing so with people you randomly meet in a random roulette that isn't a forced roulette Gauntlet as an example of above. May not work.

More so if it's not a roulette they want/planned to do. Like PVP FL, or any other roulette for pvp they may get in the future. (Or if they even have their hotbars ready in the first place)

Limits the amount of content you can do, cause as others said. New Players are more likely now a days to not have new/old side content unlocked.

And then we also have to think.

How will this interfere with existing systems and mechanics.

For one it may end up being used to ferry people into CT with one player being a CT only account.

The System would need to be reasonable. and not bloat itself or other systems.

We also have to think for who this is for.

and then for who it isn't.

and what players could potentially use it for against their or others will.