USA-Canada-USA (14 Day Quarantine) - Returned yesterday after 14 days (Thank you to those who provided me inputs). Here's my overview:
USA-Canada:
1) US side was crowded. I could not check in online so had to stand in the line at the airlines counter (few people did not even wear masks). Security check in had decent social distancing. Boarding mandated wearing masks - flight was practically empty.
2) Upon landing I had a quarantine plan sheet with details on where I am staying, etc. but wasn't asked
3) Immigration was straightforward - Provided friend's address as care of (c/o) and CoPR. Was only asked how much cash I was carrying - no proof of funds requested. CoPR stamped.
4) Customs: I had declared car for some reason - they took it out of the list saying its a separate import process. Rest was straightforward and stamped. The guy was new and said even if my old laptop died, I cannot import a new one (it has to be the old one)
14 Day Quarantine:
1) Pretty much stayed inside and followed rules to the tee (I was in one of the Marriott hotels)
2) For groceries, I did grocerygetaway. Also occasionally did doordash - Idea was to have as healthy diet as I can with some leeway for sanity
3) Did not get any calls - only two emails from the govt of canada. I called up public health to check when exactly I can leave, they gave me a date and I booked return tickets for that date.
4) I did not get SIN or Bank Account - Did not want to extend my days especially due to the looming executive order (I heard someone applied with US address - Not sure if that would work) - I also anyways mostly plan to move next year.
Canada-USA:
1) Canada side was much more organized. Mobile check in, so avoided the crowd at airlines counter. Not a single person was without mask, there was also 360 social distancing as well as wipes next to security check-in to wipe the boxes. Boarding mandated wearing masks - flight was packed.
2) US Immigration: Just took passport and stamped. Neither i-797 nor any questions were asked
3) US side landing was again crowded as you land at domestic side. Wore mask and face-shield. Took sanitizer bottles both ways.
Overall: I feel I made it back in the nick of time in this climate especially with the looming EO. For others trying to attempt USA-Canada, I would suggest wait for the EO. Like others did for me, I am open to help out if you have any questions - just ping me.