Is it actually my problem if my hitch sticks out past the sidewalk?

You're not in the wrong for parking the way you park, but the hitch is on you. If the ball mount sticks out past the sidewalk edge, that's your problem to fix. I learned this the hard way when my neighbor's kid clipped the corner of my drawbar riding his bike. Nothing serious, but I've pulled mine out ever since and it takes about thirty seconds with the key and a little muscle on the pin. The routine thing is way easier than you think. If your complex has pull-through spots, use those when you can. If it's nose-in only, just pop the ball mount out when you get home and toss it in the bed or the garage. That's what I do now and it's become automatic, same as grabbing my keys out of the ignition. Takes less time than checking the mail. There's a practical reason beyond not braining pedestrians too. Leave that thing in year round and the pin rusts in place, then you're out there with a hammer and penetrant trying to get it free the one weekend you actually need to tow. Cycling it in and out a couple times a week keeps everything moving.

If your complex doesn't have pull-through spots and the hitch would hang over the walk either way, I'd just talk to whoever manages the place and ask where they'd rather have you. Most managers care way more about you not blocking the sidewalk than wich end of the truck goes in first. Offering to nose in or pull through shows you're trying, and honestly that's half the battle with neighbors who alredy think truck guys park like they own the place.

So no, you don't need to rearrange your whole routine. Pull through when it's an option, yank the hitch when it's not, and nobody's got anything to complain about.

Thirty seconds is doing a lot of work in that math. My receiver has an anti-rattle pin with a lock on it, so pulling the mount means grabbing the key, wrestling the lock, and beating the pin loose if it's seated hard. I timed it once out of curiosity and it was closer to five minutes with all the fussing. I just back into every spot at my complex instead and the hitch sits over the curb cut where nobody walks. Never had a complaint in three years. Maybe the walk-in spots at your place work diffrent, but around here nobody crosses behind the trucks anyway.

Anti-seize grease on the hitch pin is what fixed this for me. Mine had seized up solid after a winter of sitting in there and I was out there with a hammer and a screwdriver like an idiot. Smear a little on the pin every few months now and it slides right out with a glove on. Tossing the mount in the bed became a non-event after that instead of a whole production.

Update: tried the grease trick yesterday and the pin actually slid out with one hand, so removing the mount is way less of a chore than I thought. Still deciding if I want to pull it every time though, since I've got a locking pin too. Do you folks re-grease it more often in winter, or just leave the mount in and eat the sticking-out problem?