Actually, you don't have to quarantine in New York. I've had friends land in NY and LAX and Boston and it's business as usual, they haven't been asked a lot of questions, no mention of quarantine, etc.
If I were you, I would go for it. Sounds likely that you'll get the SP at the border. Are you far from the border? I'm a US citizen but a current expat in Singapore, so it's too much of a trek for me to attempt, but if I lived in the US I would.
In case anyone finds this helpful, this is an update I received, from a connection I had that was able to talk to someone at the IRCC -
"IRCC acknowledges that they have reviewed xxxx's file and it looks good, but they are not prepared to issue final approvals at this point, due to COVID. His...
Yes, if there are no travel restrictions, you could fly into Montreal. But don't plan on that - my guess is the restrictions will be in place through the end of the year at least.
If the border restrictions are still in effect in December, then you are supposed to be traveling for an "essential" purpose only - and starting school is deemed essential. Visiting relatives is NOT. Don't take the chance - fly into Toronto.
How hard was it to get on the plane to Canada? I thought they weren't letting people on without the permits. I was planning on attempting this through a land border though flying would be preferable. Also, my son is a minor - he's the one in need of a study permit (14 years old, for boarding...
Nothing we don’t know but interesting that it made it into such a big publication... https://www.politico.com/news/2020/08/22/canada-united-states-student-visa-400107
And Canadians don't even need study permits to study in the USA! They just need an eligibility form that they get from their school. So a bit more of a process for us Americans to get there than for them to get here. (In normal times).
I talked to the CBSA today and was told that US citizens can enter with just that Phase 1 approval (AIP some are calling it). Though I'm guessing you're really at the mercy of whatever border guard you get.