A lot of those decisions fall by the wayside in the digital database world. For artist, I enter "Sun Ra," because "Ra, Sun" just looks odd (never mind that that's how he was listed in the Philadelphia white pages!). It hardly matters where iTunes "puts" the mp3 files; just search for "Sun Ra" and everything will show up.
One tip: For artists that have many different variants of their band name (think of Duke Ellington in the '30's and '40's, or, now that I think about it, Sun Ra), enter whatever the name du jour was in the "Artist" field, but enter something simple and consistent in the "Album Artist" field (such as "Duke Ellington" or "Sun Ra"); if you do that, all their work will appear together, in album alphabetical order.