Oh all that is very possible. If you remove the guild 'limitation' from the upload, you can have anyone you want pointed to your update.php, and they can upload whenever they desire.
The code would have to be changed around to accomodate, but yea, that is all very doable.
I have modified even the standard code dump, and I have it tied to my "member" names on the forum. What that does is allow them to click on MEMBER PROFILE up top, and enter further information...IE - their Race, Gender, whether that character is still active (internal flag for display purposes), and some comments on what 'gear' they need.
I take all that and auto-generate sigs at 2am each night, that way we can link them on any forums we troll...and show our changes automatically. I will add Honor to the sigs here shortly...here is mine:
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http://bladekeep.com/wow/sigs/Medar.png[/]
So yea, all of that is possible...just takes time.