Oct 13 2011 Update:
_A majority of the issues I noticed would likely not have occurred had I just waited a day or two, to avoid the inevitable time-out sort of issues expected for such massive deployments. Also note that I've located this excellent troubleshooting article on cnet._
Oct 13 2011 1:14pm Update:
As of 1:13pm, nothing. Then, as of 1:14pm eastern on Wed Oct 12 2011, iOS 5.0 showed as available through iTunes 10.5. So, time to attempt an upgrade. With 3 phones in my immediate family, and another 3 in my extended family, there's a lot of upgrading to do tonight.
iPhone #1 (of 5):
Uh oh, during upgrade process, got this error 1602 which is probably a problem with my installation of iTunes and not a big deal, but time consuming to fix:
So now attempting restore:
Oct 12 2011 2:04pm Update: it says "Restoring iPhone apps", I'll be all set. Error 1602 is apparently common and usually a client side software thing.
Oct 12 2011 3:05pm Update: turns out my upgrade may have been interrupted by incoming phone calls, looking at the phone itself during the eternal restoring apps message, it was waiting for me to answer me.com account and other wizard info, then looked like iOS 5.0 had installed, but apps wouldn't launch. Connected to iTunes 10.5 again, and it said it was interrupted, that makes sense, it's fixing itself now
Oct 12 2011 4:17pm Update: all is well, sync finished, synced a 2nd and 3rd time to be sure all went fast/smoothly, and yep, I'm at 5.0 now, nice notifications awaiting me! next stop, 2 more phones to go:
#2 (of 5):
little surprise, unknown error 3200:
tried again after rebooting the phone, and it worked the 2nd time just fine, it's done, all is well.
#3 (of 5):
This one is attached to a large music library on another computer. another little surprise, unknown error 13019, that's an easy one, just deselected all music and trying again, upgrade underway now, just need to remember to turn on music sync when done. Then the same deal as phone #1, had to restore from backup.
#4 (of 5):
This one is attached to a small music library on another computer, iTunes 10.5 offered me a 4.3.5 upgrade for some reason. Refused, tried again, this time, 5.0 offered, downloading now, so far so good with this one, although downloads seem to be taking longer and longer this evening, we'll see...
#5 (of 5):
so far so good with this one, we'll see...oops, same issue, problem with restore in the middle, tried again, it worked.
Well, in the end, 8 hours later, I got all 5 phones upgraded, (and a 6th phone in extended family), and I got iCloud working on allof them. I also accidentally wiped a calendar, and had trouble with finding export, no problem, used iphonebackupextractor.com to open yesterday's backup from my Home Server (back when the calendar was good), then exported the calendar data from that backup to an .ICS file, no need to restore phone from that backup. I then imported these entries into Outlook, which I then synced with iCloud Control Panel for Windows, cleaning up and changing to the correct account (too bad there's no merge).