I think for a lot of people it ends up not being so much of a hassle b/c you learn to slowly adjust your styling techniques and everything as your hair grows.
To me it would be really annoying to have to adjust all at once to a big change in length; thats why for my weave/braids and acrylic nails have never really worked.
My hair isn't super long, but as I get more of it I feel like my routine is getting easier as I learn more about my hair. I do get annoyed sometimes when I flatiron it though b/c my routine is suddenly different and my hair acts so much differently than normal. When its just nappy/kinky it doesn't get all in my way, sticking in my under arm or on seat backs
it is sometimes a weird adjustment
I understand what you're saying. I think some people have a limit where their hair goes from a comfortable length to just being in the way. Just go for what works for you.