CONFUSED-LOST & HELP NEEDED!

Managing Apple ID's among devices is getting more and more complicated and the "CLOUD" doesn't help me when I am on the ground?!?.  I would like some help with the problems I am having. I maybe some edumaction on how to use the cloud effectively. Overwhelmed in regards to getting the right info on the right devices.
A Couple years ago I got something from iTunes saying I needed to use an email address to log in.  My log in name from day 1 was just a username, so I put in my regualr email address thinking that this was converting my username to my email address.  That isn't the case, it created a 2nd apple ID.  So now I have to deal with 2 IDs and not sure what to use when dealing with icloud and purchases. Since upgrading my phones just about every other year and purchasing new lap tops I have noticed certain things aren't moving to certain devices. Plus, now our household has 4 iphones, an ipad, and 3 or 4 computers with itunes.  I need help simplifying and being able to know what downloads go where and what purchases are being made (4 different accounts, same credit card).
1.  Can I merge all Apple Ids into 1 main ID?
2.  How do I set up my outlook calendar and contacts to sync with my new iphone.  Which ID do I use?
3.  Picture stream doesn't seem to work and syncing in general doesn't seem to be working with iCloud. I turn it on, but nothing in my streaming folder.
4.  I have a iCloud email address and a me.com apple address.  Why? What do I use?
5.  What's the best way to have multiple users in 1 house.
6.  Is this a sign that I am now old and need to start arguing with electronic devices?
I loved the iphone and iTunes when it launched; it made everything so easy.  Now I feel like an old man wondering why I don't start using an actual calendar and postage stamps!
Please help, I need to get things back on track to focus on more important things like watching cute videos about cats in clothing...
Thanks!

Does the company that hosts the Exchange account allow users to connect with their iPhones. It isn't as simple as knowing the settings, they have to allow it and the Exchange admin have to setup certain things on the mail servers.
If they don't have ActiveSync (what is needed by them), do they offer IMAP or POP access instead?

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