I think we need to start implementing some sort of maintenance schedule and some form of change control. I don't mean filling out stupid forms or anything, but I DO think updates to LJ should only happen at specific times, maybe once a week, and should be done in a controlled fashion, with some idea of what to roll-back if something goes wrong, at least a few days of testing, etc. Same thing with upgrading the software (apache, mysql, mod_backhand for now, mod_bml or whatever the actual mod is named ;) , the OS, etc.) that runs the site.
If you're going to start doing things like offering refunds or extensions to members because of downtime, that means you're taking real responsibility for it. If you're going to do that, you have to attempt to minimize it, especially unplanned downtime. The best way to do that is to make sure that it never happens if at all possible - which means making no changes except during prescribed maintenance periods which everyone is aware of, and posting ahead of time to lj_maintenance that it will be happening.
It's ugly, and no fun to do, but it's going to have to happen sooner or later. Better now than after another round of account extensions or before people start dropping out in great numbers, or whatever.
Flame away, people, but it has to happen.