If anyone can help me navigate this, I would be forever grateful. I have been a Macrumors reader for several years but never registered until the other day when upgrading one of our devices to iOS 5. I am completely and utterly confused as to how to make this whole transition to iCloud work. My husband is leaving it all up to me since he pretty much hates technology and just wants it to work. Here is our situation: My husband and I both used .Mac for several years. His .Mac email address is our Apple ID that we use to share purchases across all our devices. We would both prefer to not have to add anymore email addresses since everyone and everything we are registered on has either his .Mac email or my .Mac email. When apple converted .Mac over to Mobile Me, we kept paying for it and so now we have mail coming to four addresses sometimes. His .Mac & .Me addresses, and my .Mac & .Me addresses. Currently we have both our email accounts set up on each and every device so we can check each others emails if asked to. (Except iPhones now, more on that in the next paragraph) We each have iPhones, but yesterday we both just upgraded to the iPhone 4S. After doing the upgrade, we just set them both up as new devices and didn't turn on any iCloud features because I was unsure of what to do. We also share one iPad at the moment for our home and traveling. I have upgraded the iPad 2 to iOS 5, but did not set up iCloud on it. We have two Macbook Pros, but only Mine has all our purchased movies and songs, etc. on it as it was purchased first prior to getting our second one which is the one my husband uses for email, web, and documents. We would very much like to be able to set up iCloud so that our Macs, iPhones and iPad to continue to use his main .Mac Apple ID to make purchases. We would also like to be able to use iMessage on our phones and would like to share contacts if possible. I read as much as I could on iCloud. It seems to work great if you are one person using devices just for yourself. If however, you are trying to share things like we are, it's a nightmare. My husband wants to just be able to have his music, apps, emails, and movies on his iPhone, he has already called me from work tonight and is giving me the guilt trip for sending him to work all night without any entertainment on his new iPhone 4S. I'm pretty much speechless as I've been researching this all night and right when I think I have it figured out, I read something else that makes me realize I have no clue on how to make this work. Perhaps I am just over complicating this for myself, but as much as we love our Apple products this has almost brought me to the point of tears.