When you change an individual track's volume in iTunes the file isn't modified, other than an addition in the tag indicating a correction factor which iTunes then uses on playback. Since the audio portion of the file isn't changed there is no SQ hit no matter how many times you alter the 'volume' setting.
The same it true when using MP3Gain on MP3 files. In that case the file is modified in that the volume flag of each frame is changed, but since there is no re-encoding then there is no SQ hit in this case either, and the change can easily be undone, also without affecting SQ. There are limits of course, you don't want to drop the level so low that you expose faults in other areas in the playback chain, and you don't want to cause clipping by an excessive increase, etc., but as long as you stay reasonable about it then there should be no hit to SQ.
I don't know if there is any software that is so gross that it actually re-encodes a file to change volume, gawd I hope not...
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