Adam more data on this... While checking sites today I found another one that was 502'ing, I don't think it was one I had restarted php on yet (don't recall at least)... So I went ahead with testing for Cloudflare conflicts.
When I updated my computers hosts file to bypass Cloudflare and connect directly to the server IP, the /login loaded and redirected to /wp-login.php perfect. I continued to test by turning off Cloudflare proxy on the domain and try viewing the website again normally, and indeed it did load and redirect properly, no 502.
So now I'm wondering how/how Cloudflare is bugging out in this way... I'm not sure why restarting PHP fixes it, nor why disabling the Cloudflare proxy and re-enabling it also fixes it. It feels like there's a connection somewhere as to why this is happening, but I'm not seeing it. Incidentally, after turning Cloudflare proxy off/on I still get 502 in my window/tabs that were already open, I'm not getting the 502 in incognito browsers now, so maybe this has something to do with something being cached as well.
I'll test by closing my browser after I post this message and see if re-opening Chrome allows the url to load or not, if not then I'll try clearing browser cache and test that.