My read on it is that, like cold calling and door-to-door sales, this is a skill. You can be naturally good at it, you can develop it, or you can be self-aware that you suck at it and do something else.

As someone who has met all his partners in places other than bars/tinder and without any dramatic public approaches like what you're describing I would say that it's important to keep in mind that there are plenty of ways you will meet people. Obsessing over the ways that you won't meet people is counterproductive.

If you mess up, you could lose your job, kicked out of your social safety net, or lose access to your favorite business.

For the most part girls will not do this. Any woman who has ever dated men eventually learns that if a man is interested he'll make it known and if you have to chase him he's not interested. For that reason most eventually give up on making the first move because those situations never go anywhere, whereas when men make the first move they do. It's not necessarily fair but it's the typical dynamic so waiting around for girls to make the first move is very unlikely to work out in your favor. Also, the thing about men being creepy for approaching is very overblown online. In real life as long as you're pleasant and polite and willing to take no for an answer most women will be happy and gracious if you approach them. Go for it!