1) Yes
2) Yes
3) Yes
4) Yes
You May have to remove and reload after changing the tags in Calibre (which is what I did while learning this very topic a few weeks ago..
) I don't know enough about Calibre to know if it will auto-update tags. I now completely skip "Tags"and use "Series" instead when I want a collection.
As for disconnection, 99% of the time it's fine, but I HAVE killed thumbdrives by not going through the complete process to eject a USB device. You can do it from Calibre, or from the icon tray next to the clock.