Nothing like listening to the nags of someone who doesn't have to do the upgrade to force one to do an upgrade without sufficient prep work, which is what I did tonight.
Flying by the seat of my pants, I upgraded four web servers, fingers crossed, data backed up, breath held and well, jumping up and down on one foot waving beagles disguised as chickens over my head.
Well, the upgrade didn't fly completely straight, and I had a good twenty minutes trying to figure out what Debian MySQL configuration file upgrades would have caused the problem. I eventually tracked the problem to an overly zealous bind-address setting, and now all is well.
This weekend will be a weekend of work, but at least the server update nags will stop.
If only I'd make the restaurant reservations...