Moving over to iPhone 6 - trials and tribulations

Bright and early this morning, I was told I received the first 2 iPhone 6 phones delivered in my town.

The plan:

• Move off of 2 iPhone 5's into 2 iPhone 6's.
• Move off of 2 iPhone 4's into the 2 iPhone 5's.
• Use covers on the old phones to keep them straightened out as to which is which.  Once a recovery is made to an iPhone 6, the cover photo will let me see which is which quickly.

Simple, right?  Here are some complications:

1. These devices are syncing to a machine with Lion.  Lion does not have iPhoto. We want to preserve the photos on all iPhones, and some have thousands of photos.
2. We are all using one iCloud ID to do photo sharing.

First I back up each phone.  This consists of:

1. Backing up to our Lion iTunes server
2. Backing up photos to a Mavericks iPhoto-based machine

• So I activate and recover each respective iPhone 6 to the backup of an iPhone 5.  Easy.
• Then I take my iPhone 4's and iPhone 5's to an AT&T store.  I wait in line for about 30 minutes, and go inside to do a phone swap/SIM card replacement on the iPhone 5's.  One will not activate!  Eventually I am told a story about how sometimes it takes up to two hours to activate.  I grab a card of a person in the store to bypass lines if the phone never activates, and head off to do more syncing.
• I then recover to the two iPhone 5's.
• Next up: voicemail.  I have no idea what the voicemail passwords are.  A quick login to the AT&T online portal to reset passwords.  I then set new passwords and get visual voicemail working.
• Then email...
• I have a corporate mobile device management system.  It is not working with iPhone 6.  It worked with iPhone 5 and iOS 8.  This precludes corporate email for now for me.
• I was surprised how much I had to use passwords in some cases, app passwords in others.  This is complicated, but doable.
• One phone would not activate.  I had to go back to AT&T, get a manager.  They did not want to let me hop the line even though the promised long activation never happened.  However, the manager remembered me from earlier (and I did have a card from the person who had been helping me) and the manager helped me outside the store.  Not letting me back in the store somehow soothed the people still in line at 8PM.  There was some kind of typo in the data entry they had to do.  Once fixed, the iPhone 5 activated just fine immediately.
• I was then trying to set up our old system of sharing photos.  We all use the same iCloud AppleID.  I use many icloud features, and every one else just shares photos and uses imessage.
• After a while into this, I was unable to put my icloud account on one iphone.  It just would not work.  I had many symptoms listed in http://support.apple.com/kb/TS4268
• I had other problems.  My wife and I would text a family member, and it looked like it came from my wife when I was texting!  This would not do.  I turned off Messages and Facetime on all of the iPhones and reset networking.  I set it all up from scratch.  It kept happening.  Eventually I did this on an iPad I have with iOS 8 and my computer as well.  THAT FIXED IT!  One of the two had somehow gotten my phone number and my wife's too, as if they were both mine.
• I had a new problem - Continuity!  A call to one cell phone was a call to ALL cell phones (and my iPad)!  I became convinced that there was no way to make this old system work.  It was an interesting cacophony!
• To fix: I went to all devices that are not my personal devices and:
•  turned off the iPhone FaceTime setting "iPhone Cellular calls"
• Handoff (under General, Handoff & Suggested Apps)
• I still could not get one family phone to use my iCloud ID to share photos.  We are not ready to turn on family sharing today.  Then I remembered my old iPhone 4 devices we plan not to use!
• I de-registered them with iCloud, turning off Find my iPhone, and then cloud services all together.
• I reset their networking, and powered them off.  They are ready to be wiped and sold.
• I went to icloud.com to verify... and saw a mess.  I had to re-sync each phone with a computer and rename it, giving it a useful name in Find My iPhone.  I had thought the recovery from backup would do this; it did not.
• I had to delete a few old items like an old computer or two that had crashed and been replaced.  
• Now it was finally time to get photos back on devices.  After wrestling my iTunes from an old Lion machine to a Mavericks machine containing my iPhoto backups, I tried to sync over photos.  The Photos area in iTunes for the device just contained a permanent spiral mark that  was like the pinwheel of death.  I waited, did other things (like eat), and came back - it was never going to resolve.  My CPU and disk were not busy in any way.
• I checked out this article: http://support.apple.com/kb/TS3697?viewlocale=en_US&locale=en_US
• I backed up each machine, then sync'ed it, and then I could copy photos via iTunes
• A new problem cropped up: duplicates!  By this time, iCloud had shared a quarter of the 4,000 photos on a couple iPhones.  This effort meant they now had 5,000.  The only way I can think of to fix this is to start over, wipe the phones, do the photo sync first, and THEN set up iCloud.  Whew.
• Other problems: in turning off iCloud and turning it back on, many other things start to sync and are turned on!  You cannot turn them off fast enough to stop this.  I had to delete Passbook data from other iPhones.

All of this took about.... 17 hours.  I have 4 iPhones, an iPad, and one computer involved.  I have some duplicate photos, and one iPhone 5 I cannot get to share photos via iCloud.  This was not a smooth process.  Advice:

• Back up each iphone to a computer with Mavericks. Back up photos to iTunes on that machine.
• Turn off Facetime, Messages, and for good measure iCloud on phones you are retiring or repurposing (once they are backed up).
• Recover the phone in their entirety, including photos.
• Clean up any old devices in Find My iPhone before proceeding.
• Then do settings like email, voicemail, and the like.  If you encrypt your iPhone and iPhone backups, these settings can pass into the new iPhone.  Why not use that advantage?
• Do iCloud enablement last.  Use the FaceTime and Continuity settings carefully.  If you make a mistake, watch the iCloud settings on the iPhone and delete any data you did not want on the iPhone.

Updates:

• Under Settings, General, About, you can rename your device.  This is a helpful tool with iCloud.
• My iPhone and my wife's have no music on them.  None.  We downloaded via iTunes match - apparently we have to start over.
• One iPhone 6 is having weird audiobook behavior - it will not restart from headset controls...
• We have quadruple (or more) photos in... our photo albums.  I cannot say photo stream at this point.  What a mess.

More updates:

• One repurposed iPhone 5 would not connect via facetime or messages no matter what.  I had a scheduled call with Apple, and they said my old iPhone 4 and the new iPhone 5 were both in apple systems as active with iMessage.  The support person said they cleared it and suggested I had to call AT&T to get them to reset things.  I called AT&T and they said everything was fine and started me through messages troubleshooting.  I said no, Apple sent me there for a reason.  They asked me to recover the iPhone 5 from scratch, and I insisted they get Apple back on the phone.  I quickly got to a senior technician who had me use xcode to dump logs from the phone - very cool! I'm told I'll hear back in a few days once engineering figures out what to do.