For those of us who may have glazed eyes and a bit of a headache from reading Sir jaybonci's excellent geekspeak report above, let me attempt a summarizing translation.
A number of major and necessary under-the-hood changes might cause Everything2 to burp and fart a bit in the near future, although the basic stuff should be OK. We can help Jay out by watching for problems and reporting them, as we have in the past.
One big thing is the operating system (Debian) that runs on the computers that serve E2 to us (servers). After some years, the OS has a major update and that time has come. Jay is changing us from the "Wheezy" version to "Bionic". The update is likely to cause problems, but will bring the advantages of the new version, increase efficiency, and may reduce the cost of delivering E2 to the world.
After that, Jay will do some magic on the database, which will take a lot of work, but is not so urgent.
This is my interpretation and offered as a public service. It may be wrong in whole or part and entirely unnecessary. Any error or omission is my bad.