My BSL hair (pic below) started breaking kinda in the middle, to about neck length. I'm also thinning, and it got harder for me to tell what was going on--I just cut my hair last weekend to a little past shoulder length. It looks a lot thicker and I know holding on to those scraggly ends wouldn't have made sense, given the number of inches I'd have needed to wait it out. I also wasn't interested in gradually trimming it up.
My hair actually looks kinda the same when I style it, just less length now. I'm getting used to it, but I miss the long rollerset coils on my shoulders. This time around I'll be taking MUCH better care of my ends. I'd say don't hold onto bad ends if they're impeding your styling options and if they're too hard to hide. I feel a lot better having alleviated the problem; trying to fix it for the last few months was just stressing and bumming me out. It's hair--it grows back. And if you nip the problem and identify what you need to do to change it, it'll be much healthier, IMO.