I also have this problem, it's been this way since I was a very small child. The earliest instance I can remember was waking up with it dislocated, walking downstairs crying, my mom not knowing what to do, and me sitting on the couch awkwardly until my dad came home which seemed like all day but I honestly have no idea, it was before I was even 5 but I still remember it.

Second time was probably first grade, was going down the slide and slipped, arm hit the side of the slide popped out before i got to the bottom, laid there the rest of recess waiting for the teachers to call my dad, the gym teacher(a former basketball coach) insisted he could do it, and i'm sure he could have, but I absolutely would not let him, dad had to leave work, came and rescued me, talked me through what he was doing, assured me that the gym teacher could help, but most importantly explained how to do it myself

from there i hardly remember it, mostly a minor annoyance, may have had the teachers help once or twice, may have done it myself, don't remember. i feel like during puberty it almost never happened, i've always had issues when raising my left arm too high over my head when stretching and stuff, where i feel it start to slip and catch it usually with a startled gasp to accompany a quick and awkward lowering of my arm

then it started happening again when i started having my girlfriend stay with me a few years ago(we live together now) i would put my arm under the pillow ,and up and sleep on it funny, both of our heads on the pillow, i specifically remember scaring the shit out of her one night as i jumped out of bed with my arm held way over my head in a very wierd fashion, it wasn't a little bit dislocated, my arm was escaping. popped(there is no better word) it back in and went back to sleep.

so yea moral of the story is it still hurts but you do get used to it, it takes about 20 or 30 times and the first couple you think you might die, but it just becomes an annoyance after awhile

i'm not a badass though, wiped out on my longboard a few weeks ago, and thought i had dislocated my hip, i didn't even come close, barely bruised it. i was terrified though, and i assure you if i ever did dislocate my hip, i would do two things, cry, and call my dad. even though he's 2000 miles away