Quickly Upgrade All iTunes Matched Songs to 256Kbps
From Macworld:
Make a Smart Playlist Create a Smart Playlist with the following attributes:
- Bit Rate is less than 256kbps
- Media Kind is Music
- Any of the following are true: (to create this conditional, option-click on the plus button in the Smart Playlist window) iCloud status is Matched, iCloud status is Purchased.
This creates a list of all your low-bit-rate files that are upgradeable—namely, ones iTunes Match has deemed Matched or Purchased.
Finally, make sure that all the songs remain selected and right- or control-click any song and choose Download. This will start the long (depending on how many songs there are, possibly very long) downloading process. iTunes only downloads 3 items at one time, but Apple's iTunes servers are generally very responsive.

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