At what length did your hair start to require a lot more work and time? For me, it's when it got to shoulder blade length. It just seems like I have to comb it more often, it's harder to reach, and it gets in the way more. Don't get me wrong, it's worth it, but I don't see it getting any easier the longer it gets. I guess you just get used to it.
if you have to comb a lot, maybe you are not using
good conditioners and detanglers...or maybe you are not
restraining your hair properly while sleeping...
or in the wind.
WHEN did my hair start requiring more & more time & effort?
ALWAYS! Only a tail brings some peace.
To more easily reach the ends of your hair as it gets longer, pull it around in FRONT of your shoulder to brush it. Either that, or bend all the way over forward and brush it "upside down".
When it was short. Seriously.
I don't think length is really a factor (once your past the awkward stage that is), it's finding out what works for your hair. My hair always required a lot of work until I found the right products to use on it. Now it's just smooth sailing