Hi Aaron,
I asked for a (long) listing with the -l (lower case "el") option, not the -I (upper case "eye") option. All you had to do was copy-and-paste. However, I don't know if it would have helped. We may be able to tell you something about the client that will help you figure out what the server is doing but we can't tell you about the server because it's not an Apple implementation of an AFP server.
I gather that you told iTunes that to open a music library on an AFP share. It's nice that iTunes is robust enough to mount the share but it appears to not know when the share is already mounted. One possible reason is the difference is case. HFS+ is case-insensitive but is case-preserving so if a process inquires as to what is mounted in /Volumes, the name of this share is given as "media." If iTunes is looking for "MEDIA" and compares in a case-sensitive fashion, it will think it's not there. Thus, if you could get the cases to match, maybe iTunes wouldn't mount the share again.
In mounting AFP shares, the Finder is case-sensitive. If I specify the share in the URL and spell it with the wrong case, the Finder reports that it cannot find the share. If I select it from the menu, it's already spelled with the correct case so I don't see how it's possible to get the case wrong with the Finder. Of course I'm mounting the share of an OS X server and your evidence suggests that the "Buffalo TaraStation NAS" behaves differently.
I don't know how iTunes deals with libraries that are on a remote share but I hold out hope that you can convince it that the share name is media. I think there's a chance that it will use the already mounted share if the names match in case.
On the other hand, it doesn't seem to be an error to mount an AFP share twice and the Finder's method of adding "-1" to the name should work to make UNIX paths unique. I cannot explain the discrepancy in the two listings though. There is another mistake in the /Volumes/media listing; the "iTunes Music Backup" directory is listed twice and the inodes match. Thus there clearly an error; it would be interesting to sniff packets and see if the error occurs on the server or the client but I'm betting on the server.
According to the one long listing we have, both shares were mounted with the authority of the user aaron. However, the groups are different and that really surprises me. This may take an AFP expert to resolve but it was my impression that the group owner of a share was determined by the server. That suggests that these are actually two different shares. Does this server share a directory that contains the "media" share? Can you think of any way that these could be two different AFP shares with the same share name?
I also want to second Jeff's — Oh, you just posted that you like Jeff's solution. That's just as well. Tiger puts resource forks in files on such filesystems and the Finder presents them as it would an Appledouble file. Also, it supports Windoze permissions, which are quite elaborate. Finally, to answer your last question, it shouldn't be possible to have a problem with samba shares on Leopard if they really stood behind their claims and froze the kernel API in Tiger.
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Gary
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"Out of register space (ugh)"
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