Some things missing- how old are they, how long have you had them..
I think we all do basically the same with our own "style". Example, my 1st set of keets was raised inside. When I started taking them out, it was into a covered kennel I cld go in w/them, bc I wanted to maintain my "bond" w/them. They soon flew directly from their brooder to the kennel. From there we graduated to the outdoor coop. I didn't do one at a time, bc I was "the one". In other words, they stayed where I was. From there, they graduated to staying in the yards on their own...UNTIL the girls began nest building & egg laying. Then all bets were off, bc there was no controlling where they wanted to nest. Where ever they went, all the boys followed.
They each have their own wrist watch and knock on the back door when it's time to go in every afternoon. (Ok, the wrist watch was kind of a joke, 4pm every day, they do knock on the back door to return to the coop. I don't leave it open to keep out those who don't belong).
My last remaining female spent the rest of the season locked up. In the coop, in the run, in the kennel, but never free, & the boys stayed in the yard. Now that she has stopped laying, she stays in the yard and is allowed to roam free.
The 2nd set are 10 weeks old - and oh so different from my 1st set. But- there's only 2 of them, they stay together, and stay near the adults. So I did not release them one at a time, either. However, I am prepared that come next spring, they are females, so they too will be limited for their own safety.
So, bottom line is how you raise them & how protective you are of them.