Playlist problems with music on a Mac.

Question

I somewhat recently switched to using multiple Mac's as my main desktop machines, all running Lion.  I'm trying to do everything "the Mac way", preferring Apple-provided apps where possible.  While im 95% happy, the funny thing is that the part that works worst is playing music.  So please school me in the Mac way of making music come out of the headphone jack.
Background: For over a decade, I've been ripping all my CDs, and storing them on a server.  That's done by converting the tracks into mp3 format, and storing them in a directory tree, one directory per CD.  The names of the tracks are very simple - they are 1.mp3, 2.mp3 and so on.  Each track hasID3 tags with album, track title (usually the movement name, like Allegro or Andante), and the artist.  Each directory contains a playlist in M3U format, cunningly always called all.m3u (as it contains all tracks in this directory). Many directories also contain other playlists.  For example, if the CD had both Bruch and Mendelssohn's violin concerti, it would probably have two extra playlists, called bruch.m3u and mendelssohn.m3u.  Or if it contained Beethoven's 1st and 2nd symphonies, it would have 1.m3u and 2.m3u.  Navigation and search is done by a series of html pages that are stored in the same directory tree, making locating music (whole CDs = directories, whole works = playlists, and individual tracks = mp3 files) quite simple.
This whole directory tree is avaiable through a HTTP server, mounted as a remote file system (for example by AFP or NFS), copies exist on some of the laptops I carry with me, and much of it is also copied onto USB sticks.
With both Windows and Linux desktop machines, this was very easy to use: point a web browser at the directory tree, available through a http server within my house.  Click on an individual track (an individual mp3 file), and it immediately starts playing (since all sensible players buffer).  Point at a playlist, and it immediately starts playing.  The same player can handle mp3 and m3u files, making the user interface simple and consistent.  There are no cache consistency problems: If I quit the player, edit the playlist on the server, and then click on the playlist again, the music player will pick up the new version.
In contrast, on the Mac nearly nothing works, and the little that works works badly.
If you click on an individual track (a single mp3 file), it actually starts playing in the Safari tab.  But that player (I suspect it's a stripped-down version of Quicktime embedded in Safari) is extremely stripped down: it doesn't even attempt to display ID3 tags and claims that everything is "live broadcast".  It doesn't react to F8, so you can't quickly pause the music if the phone rings or someone comes into my office (you have to mouse over to the Safari window and click, way too slow).  And there is no way to rewind while playing.  But at least something comes out of the headphones, and it is the track I expected to hear.
Now, with playlists, this completely breaks.  If you click on the link to the m3u file in the web browser, Safari downloads the playlist, then starts iTunes. Unfortunately, it completely forgets to tell iTunes the context, so iTunes is incapable of doing anything with that playlist: the playlist "waldstein.m3u" contains entries 1.mp3, 2.mp3 and 3.mp3 for the three movements of the Waldstein sonata, but iTunes doesn't get told that the playlist was found in the directory http://homeserver.example.com/music/piano/dg_419053, and that the relative file names are in that directory.  So there is no way to play a playlist from a web browser if it is being served by http.
Strangely, if I point Safari at a html page that is on the file system (perhaps on a USB stick or a shared server), the link between Safari or Finder and iTunes works: You click on a playlist file (either on a web page or in the finder), it opens iTunes, and it starts playing the tracks.  We'll get to the broken caching below though.
OK, plan B.  Take the whole directory (many dozens of GB, hundreds of CDs), and ask iTunes to import it all.  No problem.  iTunes is even smart enough to know that 1.m3u is a playlist (for Borodin's first symphony), containing four movements 1.mp3 through 4.mp3.  Unfortunately, iTunes is also completely stupid, and thinks that all files names 1.m3u are the same playlist. So now I end up with a large playlist called 1.m3u, which contains about a dozen symphonies, sonatas, and piano concertos mangled together.  The really amazing thing is the playlist called all.m3u, which contains every bit of music I own.  The reason I say "stupid": assuming that two m3u files that are found in different locations but have the same name must be the same playlist and must be merged is really jumping to conclusions.  But at least I can sort it by album title (usually the name of the work), and track title.  But that doesn't do anything useful.  I have probably 10 recordings of Rach3, and being presented with 30 tracks, 10 of which are the first movement, then 10 second movements ... sorting them alphabetically is not useful.
Sorting in general doesn't work: If I by mistake ever sort within iTunes, then it loses the original order of the tracks within the playlist.  And I don't want to hear a symphony in the order "Allegro, Andante, Moderato", just because that's the alphabetic order of the track titles: it works out to 3rd - 2nd - 1st movement.  And I have not yet found a way to tell iTunes to revert all playlists to the order the tracks showed up in the playlist.
If you tell iTunes to start playing in the middle of a large playlist (for example just the last movement of Rach3 with Argerich), it will happily continue playing within the same playlist.  Even across track / album boundaries!  Today I was playing Bach's St' John passion out of the giant "all.m3u" playlist, and at the end, it simply drifted into Borodin's 1st symphony.  Quite the shock, musically speaking.
The final straw is this: Once you import, iTunes wants to take charge, and it caches all the metadata (namely the playlists and track filenames).  In caching this, iTunes cmpletely forgets about any form of cache coherency protocol: just because you saw a playlist once doesn't mean that it will always be in that place, and will always have the same content.  Say I have imported at home, and iTunes remembers that the 1st movement of the Waldstein is in /Volumes/HomeServer/music/piano/dg_419053/1.mp3 (and at home that file is accessible via AFP or NFS).  Now I take my MacBook to the office, open iTunes, and click, and nothing hapens: my home server is not mounted in the office.  No problem: I reach into my briefcase, which contains a 32GB USB stick.  If I now open that playlist, iTunes starts playing it ... but now I have twice as many tracks.  Do this for a while, and you end up with N copies (for large values of N) of each playlist, and at any given moment all but N-1 of those are broken.
Even worse: Say I discover that I made a mistake, and forgot to add the last movement to a playlist.  No problem, go to the server that contains the master copy, edit the .m3u file with emacs, done.  Through a variety of rsync... scripts, the various copies on other computers or USB sticks will be updated soon.  But iTunes remembers the version it imported weeks ago.  Do I have to clear my iTunes cache every time I edit anything anywhere?  Why does iTunes even have a metadata cache, if it is usually wrong?
So, let me summarize my problem.  I'm looking for a way to click on a mp3 or m3u file that's stored via some sensible protocol (be it HTTP, local files, remote files on a shared server, or file system on portable media), and just play it.  Without storing a play list, without rearranging the play list, without caching, but with a display of the ID3 tag and a working pause key.
Here are my biggest complaints about the software that ships with a Mac:
The mp3 player embedded in Safari is missing about 90% of the function.
Linkage of playlists from Safari running on HTTP to iTunes is broken (but it works from Finder, or from Safari running on files).
iTunes insists on importing or caching playlists.  I don't need that, I have better storage mechanisms.  I want iTunes to play one track or one playlist, and then be done and forget everything it ever knew.  Is there a way to tell iTunes no never remember anything, just play the one thing I ordered it to?
If we absolutely must import and cache all playlist in iTunes, at least teach it to recognize that m3u files with the same name found in different places are not the same, and shall not be merged.
Once you sort a playlist in iTunes, I don't see how you can tell it to get back to the original sort order.
Any ideas?  Other than going back to Windows and Linux desktops, which I don't find acceptable?

Answer 1

I would also recommend that in order to ensure the person is getting the document in a format they can understand that he prints to PDF the documents.  Macs do that very easily.
OpenOffice is free and crossplatform.  If they need to edit his documents, they should all agree to use OpenOffice.