Open graph metadata isn’t pulled on Facebook until after I run that specific link through the debugger

First, this isn’t a WordPress specific question, it’s a Facebook question.

Secondly, Facebook caches pages, they don’t crawl them on every submission. If you have a URL that has already been submitted to Facebook before, then they will have already crawled it for the OG data once before, and saved it to their cache. If you later change the OG data, they won’t notice it immediately, because they’re pulling from their cache, not from the page.

The Facebook Debugger forces their crawler to pull from the page in real-time, and thus updates their cache.

Simple as that really. If the URL has ever been posted to Facebook before, then changing the OG data on it won’t take immediate effect. It’ll take a few weeks before FB notices. Using the debugger overrides that.