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OP should just submit PR and OWP. If your study permit is about to expire and you have not received AOR from your OWP I would swtch your status to visitor. I agree with the lawyer.
This is what they want to do, but lawyer say they dont have to switch status to visitor and doing so would confuse the officers
 
I’m not sure I understand how exactly I was lucky though. Two years after I went back to school, I applied to extend my study permit as my old one was expiring. Why didn’t they tell me that my study permit had become invalid due to my 9 month break from school and that I was in the country illegally? Doesn’t make any sense to me. It’s not like I was hiding and pretending to be going to school.

I even left the country in 2012 while I was still on that supposedly invalid study permit and was allowed back into the country. None of this makes sense to be honest. The only way this makes sense is if they changed the rules recently.
Please mine (SP) just expired today. I had to leave school due to some family emergencies in November 2019, my question is I now want to apply for PR so I can have my entire family (including my children) come with me to avoid any other family emergencies, I am wondering if my long break and SP expiring will affect my chances.