Greetings and salutations,
I reviewed your proposal and I am confident that I have a solution for you. Namely, Debian/Ubuntu systems suffer from package breakage. Packages gain and lose dependencies often. When you update your package tree via apt, conflict occurs: apt expects one set of packages to be installed, but instead, the archived set gets overwritten. This behavior is not exactly commonplace, but it is certainly not extremely rare either. We can try re-configuring dpkg and forcefully re-installing Jenkins or, after we re-configure dpkg, we can purge Jenkins entirely from the system and re-install it from scratch. The choice is, in the end, yours. If you wish to know more, feel free to send me a message.