iTunes Match quality upgrades isn’t just for low bitrates
I’ve seen a lot of tutorials like this one by Quentin Stafford-Fraser or this one by Jason Snell stepping people through the process to upgrade their old low-quality music to high-quality fresh version via Apple’s new iTunes Match service. All the posts I’ve read suggest the same thing: make a smart playlist showing all your matched songs with a bitrate below 256 kbit/sec (which is the quality setting for all iTunes music downloads), delete those files, and tell iTunes to get fresh copies from iCloud.
In other words, a playlist like this one:

This method, however, is missing a footnote. Quality isn’t just about bitrate; it’s also about the actual codec in use. MP3 is a very old format with problems and limitations that were addressed in the design of later solutions like AAC or WMA. Because of this, 128 kbit/sec AAC files sound quite a bit better than 128 kbit/sec MP3 files, for example.
With this in mind, I’d suggest you employ an extra smart playlist to pick up MP3 files of greater than 256 kbit/sec bitrate. These files, which won’t show up in the first playlist, will also sound better if you replace them with the iTunes Match version from iCloud — and as a bonus, the new files will even be smaller than the old ones.
Try a smart playlist like this one:

It turns out I had a few hundred of these, because back in the day I routinely ripped CDs using the --extreme LAME preset. This uses a variable bit rate codec which, for complex songs, could often average out at somewhere around 280-300 kbit/sec. I also had some rips I’d done at a fixed 320 kbit/sec. Listening to a few of those has confirmed that the AAC downloads from iTunes sound better, so I’ve deleted all those now.
So if you are looking to upgrade those old rips to pristine new downloads via iTunes Match, don’t overlook this extra trick to squeeze out a little more sound quality and save a modest amount of disk space.