First, for all my ID3 tagging [which is for every single audio file I have], i exclusively use mp3tag: http://www.mp3tag.de/en/
Next, you will need to decide the naming/tagging convention that works for you.
For me as an example, I always do this:
So I tag and make my filenames like this:
Various Artists - Voices - 02 - Who Wants To Live Forever [Sarah Brightman].mp3
Various Artists - Voices - 03 - Mama [Luciano Pavarotti].mp3
For me the above makes the most sense. YMMV. Regardless, it sounds like you need to come up with some kind of consistent system for yourself to avoid the hassles you mention.
hth and cheers,
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