Multiple iTunes IDs, can we share downloaded content

Myself, -iPhone, iPad
Wife - iPod, iPad
Son - iPhone, iPad
NAS and wifi infrastructure.
We all have Windows PCs and have been buying/downloading content for some time under unique itunes accounts/emails. The goal is to be able to share what we purchase. Also we want to load several hundred CDs into iTunes and share that among all three.
What is the best way to do this, if it can be done. Home sharing doesn't fit our use case.
Thanks, David

You could all share one account, but you cannot share items from, say, an account you yourself have, with your wife and son if they maintain separate Apple IDs and synchronise their devices to the accounts they purchase items from.

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Refer to this article:
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Hi olddawg66,
Welcome to the Apple Support Communities!
There is a new process called Family Sharing that I would suggest you take a look at.
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The second link in ingo's response is key. If you husband syncs his device on the same computer, whether under the same apple I'd or not, you can share music( each pick their own based on what they want to carry around) and pictures, and apps.
Updating apps can get tricky, as they will only update to the original apple id that bought them. But music is fine.
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My wife and I have the same exact library. When she buys something, my computer/ipod/devices are authorized to use it. We both got new laptops and we wanted to refrain from adding too much on them. I have an iMac with the music library on it. I signed up for iTunes match so that I could have my library on my devices and our Apple TV. So the question is, how can I get the same library on her devices, without uploading this library to her laptop?
Can I simply log out of iTunes on the iMac and then log in as her and sign up for iTunes Match under her ID and go through the process again and all is done?
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No, there is no way to do this at this time, and if you make a mistake trying, you can screw yourself up and end up locking yourself out of Match.
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I recently learned about this the hard way when my son came home from college and used his Apple account to re-download a single TV show on my computer. When I logged in later to try to use Match, a splash informed me I would have to wait *90 days* to switch back to my AppleID! Luckily, I emailed the iTunes store and they were able to reset it. I'm not sure if they have single incident forgiveness policy, if they were able to see exactly how much money I've put in their pockets over the last couple years, or if they were simply smart enough to realize that *not* doing so could only lose them money in the future.
Add to this the fact that you now "associate" (with a different definition) your AppleID with your *user account* to use cloud services, and you have three different and inconsistent ways your AppleID is used on a computer.
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Multiple iTunes IDs, can we share downloaded content

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