Hi, I created a little app using C#, .NET 3.5 and WPF. Whatever. It's like 20 lines of code. It simply creates a .m3u file for each .mp3 file in a given directory structure (your shared NHL10 sounds over the network).
This allows you to use playlists over the network instead of copying the custom music files using CDs. (I actually don't have any CDs and you can't rip files from DVDs/USB drives). Oh yeah, and I added a wipe playlists function that will wipe only the generated playlists so you can undo whatever the app has done.
Here are some screenshots of the tool:

more pics : 2.png, 3.png, 4.png, 5.png
Edit : link fixed
And here's a download link for the actual mini-app. You need .NET 3.5 in order to run it (Windows only)
NHL10_Xbox360_PlaylistMaker
See those threads for some actual custom music:
NHL 11
NHL 11 OS Sound Pack (SEPT 1 RELEASE)
NHL 10
TNKNGM & Jokah NHL10 Music Files
NHL 10 Sounds Thread
Instructions
1. Manually create playlists for multiple shared audio files (ie., 1 for intermissions, 1 for BIP and 1 for Penalty Home) using your favorite media player (make sure to save them as m3u).
2. Apply those manually created playlists to the whole league Intermission/BIP/PenaltyAway custom sounds inside your game.
3. For Introduction/Goal/Victory folders:
3.1 Use the tool in order to generate the .m3u files
3.2 Apply each of the generated playlists to its team Intro/Goal/Victory custom sound.
Note that you'll get a buttload of playlists if you just run the tool over the root of the folder containing the 300+ songs. So I suggest doing this in batch, folder by folder.
So, all in all, it's pretty much the same process has applying mp3 files from the xbox HDD, except that you don't need the actual files ON your xbox - you can rather use the shared m3u playlists over the network.
Actually, the music pack makers should use this tool and provide the m3u files with their packs. The tool should remove the hassle of creating every playlist one by one.
Enjoy!

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