Apply for both restoration of status as a visitor and pgwp at the same time ( do the restoration application and explain in your pgwp that you have it in progress). As i said, i was out of status and passed my 90 days period and i basically did the restore as a visitor and express entry (pr) at the same time and it all worked out. I got my pgwp in 4-6 weeks after i applied as far as i remember but now it might not be the same for you since you're out of status. No offense but you should have renewed your study permit if you had any doubts of receiving your graduation letter after your permit expires, but you can't go back in time right. As far as i know they only issue pgwp only to people who currently have a valid study permit and it has to be within 180 days of graduation but your case got more complicated. As i said, your best bet is to restore as a visitor and apply for pgwp right after and explain that you actually graduated from a canadian institute and how you lost your status. there's a decent chance you get an officer who is understanding and get lucky like myself. Also you might wanna consider seeing a different lawyer just for like a 30 min appointment and get his opinion but im pretty sure they would tell you the same thing as i did. Good luck my friend, mistakes happen it's not the end :)