One iMac, two devices, and confusion

I have an iMac. I sync to two different devices: an iPad Mini and iPod Touch. There's completely different content on the iPad Mini and iPod Touch, so I set it up with two different iTunes playlists, as per Apple's instructions.
Problem is, the podcasts are incorrect when I sync. Is there some kind of guidebook for users who have two different devices with entirely different iTunes playlists?

There we go...
On the first user-account iTunes Match is working fine. No problems on that.
What I did on the second User Account:
1. I logg on to the second user account
2. starting iTunes
3. selcting iTunes Match and then "activate"
4. after I enter the corresponding Apple-ID, iTunes Match starts to compare the lokaly saved music with iTunes Match which takes about 10-15mins (Step 1 through Step 3)
5. after that, it shows me the button "finished"
so far so good
If I press the button "Finished" it jumps back to the initial Screen, where it starts over with Step 1
That loop never stops.
So there is something not quite working at all.
Is that better to understand? I don´t think, that screenshots will help at all, as there is now difference to the coorect messages. There are no error messages

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    There we go...
    On the first user-account iTunes Match is working fine. No problems on that.
    What I did on the second User Account:
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