Transfer iTunes purchases to android phone

Hi All:
I understand the dangerous political territory I am now entering, but I thought I better ask my question here since I haven't found the solution elsewhere.
I have an iTunes library of purchased music on my (7th Apple) computer and an iPod. I have been an Apple customer since the 90's.
I also happen to have an older Android phone because I cannot afford an iPhone and its higher data plan fees (on my carrier).
I cannot find a way to transfer all my music (using DoubleTwist) - songs downloaded off of iTunes cannot be authenticated/transferred.  Which is ludicrous. I paid for them, why can't I listen to them?
Thanks for any tips.

I don't want to get/buy better versions of the music, I just want to play, what I have bought, on the machine of my choice. I used to carry a nano around but it was stolen and I figured: hey! why not my phone!
Not sure why I can't authenticate my phone to replace my nano, regardless of it's manufacturer. Ethically, I should be able to!
There are hundreds of tunes so burning cd's isn't a choice.
Thanks anyway,
Tannis

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