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I've been living in Canada since March 2020, this whole time I've made sure that I was okay with IRCC, I'm currently on my 4th visitor Extension, and they were all approved. (so yes, there was a legal/right way to do it)

I think you dropped the ball and 99% that you will not be allowed to enter Canada, regardless of your Valid Visitor Visa.
 
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If I show my University enrollment, results, valid return ticket, would it help?
Might be you can try your luck
Reason your chances are slim because of your earlier overstay and as mentioned by you your family is in Canada on Refugee Claimant status, chances become less

Good Luck
 
The only thing you can do now is buy a ticket, get on the plane and hope they let you in at the border. Or the worst could be they tell you to get on a plane back to your home country. You only loose your air ticket. So if you willing to take that risk of loosing your air ticket money and also few days then give it a go...To be honest you never know who you meet at the border so you can just be hopeful and try.
 
I misspoke, I HAVE a valid TRV (Tourist Visa), I thought you meant an ARC.

Plus, when they asked me to leave the country, they deliberately did not cancel my TRV, they told me that I need to leave right now, but I can come back later.

With a departure order, don’t be surprised to find that, despite your trv not being physically cancelled, it’s been cancelled in the system.
 
With a departure order, don’t be surprised to find that, despite your trv not being physically cancelled, it’s been cancelled in the system.
The only thing you can do now is buy a ticket, get on the plane and hope they let you in at the border. Or the worst could be they tell you to get on a plane back to your home country. You only loose your air ticket. So if you willing to take that risk of loosing your air ticket money and also few days then give it a go...To be honest you never know who you meet at the border so you can just be hopeful and try.
Might be you can try your luck
Reason your chances are slim because of your earlier overstay and as mentioned by you your family is in Canada on Refugee Claimant status, chances become less

Good Luck
I've been living in Canada since March 2020, this whole time I've made sure that I was okay with IRCC, I'm currently on my 4th visitor Extension, and they were all approved. (so yes, there was a legal/right way to do it)

I think you dropped the ball and 99% that you will not be allowed to enter Canada, regardless of your Valid Visitor Visa.

BTW, I arrived in Canada, a week ago. WAS allowed to enter normally on my old Tourist Visa. Didn't have any issues. Plan to leave normally after my stay of 2 months.