Alright, my experience:
I had hair, with what sounds like a similar texture to yours, down to my waist until I was 24. Like you, I always wore it up. Then I decided I wanted a change and had it cut into a bob.
It caused a kerfuffle at the salon as it was such a drastic change. The head stylist did it, the other hairdressers gathered round and watched...
So...the first cut was good, but all trims after that were done worse, even though I went back to the same place and asked for it to remain exactly as it was, just shorter.
The weight of the longer hair had had more of an effect than I had realized. When long, my hair was slightly wavy, when short it desperately wanted to turn into frizz, meaning a lot more effort daily needed to tame it. If I didn't do anything special after washing, then it looked like Wendolin's (spelling?) hair out of Wallace and Grommit.
Even when care was taken, instead of the hair curling in at the base on both sides, as it was meant to, the underlying curl meant one side would flip direction as the day wore on, ending up with one side curling under and the other side curling out, which looked ridiculous.
I had to get trims far more often, as you can get away with a lot less work on your hair when it is long and worn up. This obviously cost more time and money, which could ill afford, and this was particularly annoying because I wasn't too happy with the result of the trims anyway.
Finally, and this was the most important for me: only when I couldn't easily pull my hair out of my face did I realize how important that had been for me. Pulled back it was fully out of the way, not falling forward and in the way, as it was with a bob. The hair at the sides of my face felt so intrusive, like having - I don't know - afghan hound's ears (?) at the side of the face.
I got it cut much shorter, because that cut had been so unbearable, and kept that up for a couple of years, but then grew it back out, which took forever, and now have bum length hair which I always wear in a plait.
Tl/dr: if it works for you as it is and you hadn't been considering a change then don't make a change!