Multiple devices: Apple/iCloud IDs and iTunes

Hi - I have a headache trying to figure this out reading articles on line.
Can someone please provide a simple explanation to do the following, and being very clear on Apple ID vs iCloud ID? I can't believe this is so complicated, but judging by the number of stories on this, Apple really needs to put out something step by step.
Currently I have one Apple ID and one iCloud ID, using the same email address, and also is the same as my iTunes account. I have a iPhone 5 tied to this, and manage my wife's 7th gen Nano using the same.
I just got my son an iPhone 4S. I would like to manage all of the content on his phone (music, apps) off of my account, but I'm reading that he need to have his own Apple ID and iCloud ID to use FaceTime, iMessage, track his phone location, and to keep his iCloud documents separate from mine (which makes sense).
So would someone be able to give me a quick step by step as to what needs to be done where on his phone, and if I can keep my email logged in on iTunes, or if we need to log in separately will we still have access to the same library?
Thank you for any direction you can provide.

My iphone 5s = apple id 1
Husband iphone 4s = apple id 2
My ipad = apple id 3
Son #1 ipad mini = apple id 4
Son #2 ipad mini = apple id 5
For iCloud.. Not quite, you want the same ID for iCloud on your phone and iPad so you have the same info on each. (so perhaps ID 1 on both.
But if you want to share your music (assuming lets say its your ID 1 that has the iTunes account), you should all use ID 1 for iTunes.

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I work in an office that is all mac based and have mac computers at home. I have an apple ID and iTunes account for personal use where I purchase books and music and I have an office apple ID and iTunes account to share calendars with colleagues using iCloud and purchase work related apps like upgrades to operating systems, etc.
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One family member has an iPad2 with one Apple ID that is authorized in iTunes on a Win7 laptop. That laptop has one Windows user account. Some apps, books, etc were purchased with that iPad2.
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My wife and I both have iPhone 5's (soon to be 6's) running iOS 8, I have an iPad (v2) running iOS 8, and my wife just got a MacBook Air (running Mavericks, soon to be Yosemite). We also have Apple TV (v2) running the latest OS. That's five Apple devices shared between a husband and wife (not counting my two-year-old's unsupported iPhone 4 used for kid games).
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New At This
PS - I am very computer literate and can implement complicated solutions if necessary, but I am not familiar with any cross-device sharing options or even the OS X interface at all.

here's a mockup of sorta what I'm going for:
http://imgur.com/pN70P
just not sure what elements would be most logical to start from!

Multiple devices: Apple/iCloud IDs and iTunes

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