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!