Managing iTunes library size on my MacBook Air

I'm trying to figure out an efficient way to manage a copy of my iTunes library using iTunes Match & am hoping somebody can help.
I have a 20000 song library that lives on my iMac (which has a 2TB hard drive). That library is backed up regularly and is the main home of my music. I also have a MacBook Air. Thanks to iTunes Match, if I'm somewhere with my Air and I want to listen to something, I can download it out of iTunes Match and have a local copy on the Air. This is great, since obviously my Air can't hold all that music.
But, over time, the local copies of songs on the Air start to take up a significant chunk of space. I'm trying to figure out how to remove music from the Air (but NOT iTunes Match, of course!) in a methodical way to manage that. I made a smart playlist of songs I haven't listened to in the last six months on the Air, and selected all the songs that were local, but I can't seem to remove them from the Air from that smart playlist. My thought was I could do that periodically so that I'd have things I'm listening to lately on the Air but other stuff could be removed (& of course I could grab it out of iTunes Match again if I needed to).
This would be super useful since I spend a lot of weekends in a rural area where my Internet connection is slow and volume-capped - I have my Air with me then and can easily stream music to a stereo via an Airport Express.
Any suggestions? I realize I could just delete all local songs in one fell swoop from the main Songs listing, and then redownload some playlists while I'm in the city with my better network connection, but that seems like a bit of a pain.
Thanks!

Hightlight the songs you wish to delete and type Option+Delete on the keyboard.

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