Questions on managing iTunes content and devices?

I've been a subpar iTunes user for several years now and I figured it was time that I just started asking some questions in order to get help. I love all my different iOS devices, but at times it seems that it's extremely difficult to manage content amongst the devices as well as my different computers (I use a PC for personal use and a Macbook for work.) My wife also has her own iOS device (Which we just use my AppleID on to keep all purchases under a single account) and a PC. So it seems like a constant juggling act to keep my content properly managed.
The new iCloud stuff looks like a wonderful step in the right direction for helping manage content on my different devices, but I'm still a little curious about the best way to go about storing, sharing, and accessing content. So all that being said, here's my current setup and questions.
First of all, I have my iTunes Media Folder on set to save everything to a Network Attached Storage I have at my home. This is the version of iTunes that I run off of my PC, which I guess I would say is my primary source of iTunes usage and how I generally choose to manage my content and move things to and from my iOS devices. Everything works out pretty well until I try and manage my content on any other computer.
Creating a consistent storage location on a NAS
My first basic question is, "Is it possible to have multiple versions of iTunes on different computers point to the same Media Folder?" If I could have all of my iTunes folders work off the same Media Folder that would probably help cut down on the confusion. However, I'm not exactly sure if this is just a matter of giving them all the same path to use or if there's additional permissions and things that must be setup. Also, what happens if I decide to purchase content through iTunes and I'm not connected to my home network, so the content cannot be saved to my NAS? Does it save to a default location that I can just later move to my NAS?
Home Sharing
What exactly is "Home Sharing"? I've read a little bit about it but I'm not 100% sure what it actually gets me since I already have a NAS. Is this what I need for setting up multiple computers to share the same Media Folder? Do I need this at all since my data is located on a central NAS on our home network?
Syncing devices from multiple computers
One of the biggest headaches I get with trying to manage content across multiple computers and devices is that I have to use one specific computer to Sync and Manage content on a device. For example, I have my iPhone synced to iTunes on my PC so I can edit and manage music on that device from my PC. But if I'm at work on my Macbook and decide I want to make some changes to Music I have there, then I have to sync my device to the Macbook, effectively wiping all the current content on my phone. Is there no way around this?
iCloud Questions
I have content that I've purchased on my iPhone or iPad and want to download it from the cloud to my PC or Macbook, or my wife's computer. Do I have to "repurchase" this content in order to do that, or does it just download directly for free since I've already purchased it before?
I apologize if any of these are "silly" questions. I've tried to read up on this stuff but I still have difficulty completely understanding it.

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Welcome to the Apple Community.
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Hi there.
I have the same problem, and its annoying. In iOS7 I was able to delete all the music that i played via streaming, and I play music like that 98% of yhe time. In iOS 8 i can only delete music that I have explicitly download but the streamed one seems to be hide.
The only solution to this, that is a waste of time is to turn of "show all music", see which music is already downloaded, downloads manually and the erase it.
Hope Apple release and update to fix this problems

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After hitting cancel many times, on the quickcam install popup, it eventually aborts the install completely.

good gracious, Joshua ... you're actually the
b second
person i've seen report this ...
the family cat once managed to overcome something like this. will the same trick work for you?
the family cat, "Upgrade from 6.0 to 6.0.1 -> broken due to Logitech QuickCam", 01:48am Oct 26, 2005 CDT
keep us posted.
love, b

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This article may help
http://ipod.about.com/od/advanceditunesuse/ss/Multiple-Itunes-Libraries-One-Comp uter.htm

Questions on managing iTunes content and devices?

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