Stop calling it brakeless!
It is a drivetrain brake!
I don't pull kids in a trailer yet so I can't comment on how hard that would be with a drivetrain brake. However, I would most likely use a handbrake when doing it.
Drafting people without handbrakes is perfectly fine.
I have no idea why that would be irresponsible.
Going 50 miles plus so far has been fine without handbrakes.
Sure, there are situations where a brake would make life easier but the same is true for gears or engines or recumbents and yet I don't ride those either. It is not a convenience thing!
Is it a style thing? Yes, of course it is! The riding style derived from riding without a handbrake is much different in most cases that that of someone using a handbrake. Does it look better? Yes, it does! Does it feel better in your head? To me it does! Of course there is nothing that a bicycle without a handbrake can do that one with a handbrake can't but that fluid fixed riding style that we all look at in videos on the internet is easier to acquire when one is forced. It also makes you more careful!