1. You mean I797? When is your current I94 expiring? Do you know if I94 was extended?
2. They are right in one way but still you can tell them that you can commute daily so that the status is maintained with same I94. This is must because we might end up not able to get stamping this year.
3. I am also trying but seems no sign(saw some EU one consulate in one country but not others/many). I want to get H4 done before dec but not sure when the consulates will open. I see dates for Toronto for 2021 Jan and Montreal for 2021 Jan-Feb.
I could see sometimes the appointment before Dec at Montreal but no idea if consulates will even open by Oct/Nov. No updates on below sites - watch this space to track:
https://ais.usvisa-info.com/en-ca/niv/information/announcements
https://ca.usembassy.gov/news-events/
4. No hurry for the purpose of stamping but you need the original to cross the border without headache.
5. I enter my last 5 daily visits. They dont really worry on these. So just enter last 5 day trips.