Hi everyone, I just wanted to add onto the compendium of anecdotes on here for flagpoling so that it helps others looking to flagpole in the future.
I left early around 5 AM to get to the Rainbow Bridge border and got there around 7:30 AM. I went inside the office and told the officer that I was there for flagpoling, and they said they weren't accepting flagpole applications that day. There was no one else there, so I'm not sure why they didn't let me flagpole (they said that they had other higher priority applications, whatever that means). Would not recommend going there because the officers there seemed like they didn't even want to interact with me (though I might be biased because they didn't let me flagpole).
After this, I decided to try my luck at the Peace Bridge border (Fort Erie). I got there by car, but I decided to complete the flagpoling process by walking. It took me a long time to figure out where to go because I was walking and got some wrong directions, so I got to the bridge around 11 AM. After that, I crossed and got to the US border to get my flagpole notice. The officer there took my passport and fingerprints and asked me a few questions about where I live, what my current status is, if I had ever been in the US etc. He then gave me a piece of paper that had my information on it and had "FLAGPOLE" written in the middle.
After this, I headed back to the Canadian side where the officer asked for my ID and why I was there. I gave them my passport, study permit, and flagpole notice. They then gave me a slip and redirected me to the immigration office or whatever it's called. I walked to the office and handed one of the officers the slip I got earlier, my passport, and the flagpole notice. Later they called me and asked me for all the documents for the PGWP application. After they were done looking over them, they called me again, took my biometrics, and asked me to pay. After payment, I received my work permit. It really only took around 20 or so minutes to get my work permit from when I submitted my documents. The main bottleneck is travelling. The officer who processed my application was really chill (was joking around while he was taking my biometrics lol) so I would recommend this location (assuming you get a similar officer).
I was in a situation where I had actually overstayed my welcome here in Canada. My last semester was Fall 2021 but my graduation got delayed to May so I stayed in Canada for the entire Winter 2022 semester without actually being a student (pretty sure that violates my study permit conditions). That's the main reason I decided to flagpole. I had an explanation letter prepared but they never asked me anything about my Winter 2022 status so ¯\_(ツ)_/¯
Tl;dr I would recommend flagpoling if you have extenuating circumstances and aren't sure if you followed all the requirements to be eligible. Personally, I don't think it's worth the effort to go all the way to the border unless your job requires you to have a physical work permit before you start or something.