How to contribute upgrade reports: https://www.debian.org/releases/bookworm/amd64/release-notes/ch-about.en.html#upgrade-reports
Debian operating system
Debian is a free operating system (OS) for your computer. An operating system is the set of basic programs and utilities that make your computer run. Debian provides more than a pure OS: it comes with over 59000 packages, precompiled software bundled up in a nice format for easy installation on your machine.
For point 4: Just use “reportbug” on the command-line (no idea if there is a GUI too).
reportbug-gtk
Didn't know this option exist, too bad it not mentioned on the wiki page for reporting a bug) a command line tool comes with it's own set of problems IMO, and even that does not compete with the ease of just reporting in web browser.
I have lost count of the number of bugs I didn't report or didn't add information to because of their painful mail based bug tracker.