Save Me from Myself: Cut the Hair, or Let it Grow

With all that's going on in the world, I realize hair is the last thing I should be worried about, but I'm posting this anyway. I've been pondering cutting my hair (I know, not life altering, but it's on my mind). I cut it off quite short several years ago and then went back and forth with growing it out and cutting it off for a few years. About 2 years ago, I decided to just let it grow and it's been doing so with trimmings and couple inch off haircuts since then. I know it's just hair, and it always grows back, but I thought I'd get opinions. Should I let it keep growing, or should I cut it off again?

The 2nd and 3rd pictures aren't exactly fair, as I have no make up on in the "longer hair" shots

Here's where my dilemma comes into play. Having it longer I can easily pull it back (which I often do as illustrated above). The problem is, since I can pull it back, that is what I'll do 85% of the time. Then I look sloppy and unkempt, which is fine when I'm puttering around the house, but I do have to leave the abode. I like the versatility of long hair, but having curly hair (which isn't as curly in the pics as it actually can be) is a real pain in the rear, and having thick, curly hair - well, that's not so fabulous either. It can look better than it does in the pictures above, but it usually doesn't as I don't take the time with it. When it's shorter, I can get away with doing very little and still have it look okay... however, growing it out again is nothing short of torture, when I decide I've had enough of the shorter do. So, if you're willing, I'm looking for usable input. I'll even make it easy with a poll, or feel free to leave thoughts in comments. Thanks in advance!