By adding the update as a dependency, whichever version of the update.esm each User actually has on their system will take effect.
No, it won't. In the event PluginX.esp overrides the same form Update.ESM updates, PluginX.esp will 'win', entirely negating the changes regardless of whether it's dependent upon Update.ESM or not. This can go
both ways.
A) http://i.imgur.com/kUFro.png
B
) http://i.imgur.com/DlSlx.png
C) http://i.imgur.com/z8Dgi.png
D) http://i.imgur.com/y9Phu.png
The bottom line is that, while the ground is still moving underneath our feet, we need to compare/contrast all the overrides to Skyrim.ESM forms in our mods against the current Update.ESM to prevent conflicts any degree of certainty. Thus, as always, it's best to do things with as few overrides as possible.