If my objective was to delay forced upgrades as long as possible, to minimize time spent on configuring the OS and applications, and to keep my workflows stable, I would move directly to Big Sur. I also would do the move before Apple launches Monterey because the Big Sur installer probably will become unavailable directly from Apple not long after Monterey launches.
Haven't found time yet this week, but I have decided to bite the bullet and install Big Sur after installing my new 2TB internal drive.
Like it or not, eventually I'll have to move to APFS and Big Sur or newer, and it sounds like now is a good time to do things.
I still cringe at having to port over all of my applications, and trying to get some things working that I know will break. And I definitely don't have time to do things right now, but as time goes along it will only get worse, so might as well get things over wth.
I am also nervous about how CCC works, but if anyone can make this entire process less painless, it has to be Mike Bombich!
If I can get my SSD in today, and maybe get Big Sur installed, and then get it hardened and a few basic apps, then I can worry about a full migration later. But just to get things up and working and somewhat secure would be a big load off.
We will see how all of this unfolds...