One apple id two different users

I was the "original" purchaser and user of iTunes music.  Had music on my desktop (then laptop) and iPhone and Nano and iPad Mini, etc.  Many years ago I also got my husband an iPod.  We just used my Apple ID and manually added music to his iPod since he and I have mostly different tastes in music.  It wasn't really much of an issue back then.  But since then he now has a Mac Mini and a new iPod Touch.  His Mac Mini has it's own library of music which is obviously different than the library on my MB Air.  We have "my music" and "his music" most all of which has been purchased from iTunes under the one Apple ID. I keep all of our mobile devices set to sync manually so there's no unintentional "cross mixing" of our music. Obviously in hind sight I should have setup his own Apple ID for all of his music back then, but that's a bridge already crossed.
So what's the problem?  It started as one thing but has morphed into an additional thing...  He was getting confused/irritated that on his iPod he was "seeing" "my" music which he didn't want to see or play.  I did some googling and found the setting to turn off so that he would only see music that was actually ON his iPod rather than all purchased music.
Then the second problem came up.  He had copied most everything from his library to his iPod Touch, and certain songs would play for awhile and then the sound would stop.  Music would keep moving - but no sound.  Several trips and phone calls and apple support help couldn't figure out the problem.  It was not hardware related.  I now think that the problem is that the music that stops playing is Protected AAC music and that is causing some squirrelly things to happen.  I found a site that explains how to change this protected music to purchased music using iTunes Match.  And I am not averse to doing that.  But I am so unclear about how iTunes Match would work with both his library and mine that I'm not ready to do that without some input and guidance.  I have two scenarios I would like help with:
Ideal Plan:  Set him up with his own Apple ID but he still has complete access to all of the current music that he wants including getting the protected music to be purchased music so that it works.  In the future all of his purchases are done under his Apple ID.
If That isn't Possible Plan:  Use iTunes Match to change the protected music to be purchased music so (hopefully) his iPod Touch won't stop playing those older protected songs.  And I think I'd like to use iTunes Match for my music library as well because I put music on my iPhone and it takes up a lot of space.  Would rather be able to access it through the Cloud rather than have it all physically on my phone.  But what next?  I certainly don't want to see all of his music and playlists on my phone, and he doesn't want to see my music and playlists on his phone. 
If I ...
a. setup  iTunes Match on his desktop to fix the protected music problem, then
b. copy everything to his iPod, then
c. turn Match off on his desktop and iPod
   what will happen if I
d.  setup iTunes Match on my desktop and iPhone - will I see all of his music too which I don't want to do??
I am so confused and I'm not sure my questions make any sense to anyone else.  But if anyone can point me in the right direction for a solution I would be extremely grateful.
Thanks for any tips or solutions.

I understand.  But "his stuff" isn't on my machine so iTunes Match wouldn't find "his" music to match up.  It's only on his machine.
Marcy,
Match looks for stuff to upgrade in your purchase history, not on your machine.  In fact, to make the upgrade work, the first thing you have to do is delete the DRM version!
Here are the steps for using Match to upgrade (the reference doc is  iTunes Store: iTunes Plus Frequently Asked Questions (FAQ) - Apple Support ):
Can I upgrade my previously purchased music to iTunes Plus?
Yes. If you subscribe to iTunes Match, you can download your previously purchased music again in the iTunes Plus format. To do so:
You need to delete the original DRM song from your library first. Doing this enables you to download the song again in the iTunes Plus format from iTunes in the Cloud.
Click the Purchased tab in the iTunes Store.
Click Music.
Locate the artist of the song you want to upgrade.
Click the iCloud Download icon next to the song you want to upgrade.

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