Burn your music to CDs (or one CD RW that you can delete and reburn over and over again) and rip it to each of the computer's iTunes- this will get rid of all DRM- there are other ways of syncing, but they don't get rid of DRM, nor provide a backup as a side-effect

Ultimately it comes down to merging iTunes music folders on different computers. MacMost podcast, episode #148 explains multiple technics which can be used to automate the process. Look it up on iTunes Store

While you are correct in that degradation does not occur due to D/A/D conversion signal degradation will in fact still occur. Protected music files purchased from the iTunes Store are already in the AAC format. While AAC is far superior to MP3, it is still compresses music using a lossy algorithm, so any music purchased from the iTunes Store is already degraded relative to the source material.

Using iTunes to create a CD of purchased music will not result in a CD that is on par with a commercially purchased CD that does not contain digital music files recovered from lossy music files. Therefore, circumventing Fairplay by creating a CD of purchased music you only accomplish storing a music files with portions of the original signal missing despite the red book format. Re-ripping those songs to iTunes will further degrade and the final (ripped) music files will be of lower quality than the purchased music that was already degraded.

The only way to insure the maintenance of quality across multiple computers is to purchase CDs and rip them in the format and bit rate of your choosing, otherwise you are at the mercy of the labels that more often than not offer downloads exclusively in the archaic, inferior MP3 format save at the iTunes Store.

In insomniac91 ’s case, perhaps s/he should investigate authorizing the music on their multiple Macs. If I recall correctly, as I do not now nor ever plan to acquire music through downloads, protected music purchased from the iTunes Store can be authorized on up to five computers. As to syncing libraries between computers, iTunes provides no means to perform such a feat. iTunes simply does not exist for the purpose of maintaining multiple media libraries. Therefore, short of someone having created a third-party utility to sync libraries across computers, doing so is not difficult, but can be very tedious. Unfortunately, with the RIAA SS perpetually on the lookout for what they broadly define as piracy, quick fixes for the issue insomniac91 wishes to resolve may be nearly non-existent.

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“Cannot run out of time. There is infinite time. You are finite. Zathras is finite. This is wrong tool.” 2.3GHz Power Mac G5/8GB/2x1TB HDD/OS X 10.4.11/30-inch ACD, 60GB iPod (Color)

and many people do in fact use lossless audio codec

Many people who are audiophiles will download low quality music in the first place for two reasons, 1, what you call low quality music is actually pretty good quality, 2, iTunes is a great tool for downloading music so there is no reason to use an inferior tool while superior quality may not in fact be available.

All audiophiles do not have to fit a certain stereotypes, they can be different, the same for bibliophiles, videophiles, and every other 'phile' out there.

and by the way- what did you mean when you said 'like your posistion on OS X on generic PCs?