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Updating from my experience is not Russian roulette. It always requires manual intervention and drives me mad. Half the time I just wget the new zip and copy my config file and restart nginx lol.
Camera upload has been fantastic for Android, but once in a while it shits its brains out thinking there are conflicts when there are none and I have to tell it to keep local AND keep server side to make them go away.
The update without fail tells me it doesn't work due to non-standard folders being present. So, I delete 'temp'. After the upgrade is done, it tells me that 'temp' is missing and required.
Other than that it's quite stable though... Unless you dare to have long file names or folder depths.
This could be it, but I also remember reading once it might be something to do with php.ini timeout settings too