HLDJ works..! Sort of.

[TooManyCats]

Every time I launch TF2 and play songs, the first 3-7 songs work just fine, absolutely no problems at all. But, after those first few songs, something weird happens. I press F1, and instead of the song playing, all that plays is an echo of whatever noises I'm hearing, creating an obnoxious noise for everyone. If I wait 1-5 seconds, then press F1 again, the song plays like it's supposed to.

But the problem gets weirder. After that song is over and I try to play a new one, the same problem occurs; now, however, I must wait around 15-20 seconds before being able to play that song properly.

Here, things get mixed up a little. After around the 15 second waiting mark, choosing a new song then pressing F1 to play it 15-20 seconds after the last one ended results in the same song being played, rather than the echo occurring, or the newly selected song working properly. Every now and then, the echo occurs anyway after pressing F1.

With each song that I play after the problem starts, the time is multiplied; around 3-5 songs after the problem begins, I must wait over 30 minutes before playing a new song. Once it hits that point, I know I've chosen the last song I'll be able to continue playing; I don't even wanna know how many hours I'd have to wait before being able to play another song after that. After I've selected that song, (Let's say the Super Mario Brothers theme,) no matter what song I choose next, all that will continue to play for several hours is the Super Mario Brothers theme. I'm sure if I waited 3-5 hours, one of the songs I selected would be played, but at that point, I'd probably have to wait 10-20 hours to play a different one... Quite an annoying problem to have.

So, any idea how to fix this?

1) Does HLDJ launch the game correctly for you?
Yes.
2) Does "HLDJ Loaded Successfully" appear in console on starting the game (with no errors)?
HLDJ loaded - some files could not be written ( 1 error ) !
Shame it doesn't tell me what that 1 error is. Maybe it's this, in red?
FS: Tried to Size NULL filename!
Whatever that means.
3) What is the console output after selecting a song, or issuing other HLDJ commands such as "hldj_next"?
Host_WriteConfiguration: Wrote cfg/hldj_cmd_c.cfg
Loaded : [Song name here].
4) After creating your own local server and enabling playing of audio files:
4-a) Load one of the sample audio files and perform a search of your Steam directory (without stopping HLDJ) for the file "voice_input.wav" - does it show up, and if so, where?
I performed a search of my "tf" folder after doing this. No files with "voice_input" in them were found.
5) Does voice normally work for you? If not, or you do not have a mic, have you remembered to set up any applicable options in your operating system and/or the game?
Yes, it does.

[Renegade]

voice_input.wav will show up in your "team fortress 2" folder, it's there, otherwise nothing would ever play. But I doubt that's the problem.
Based on the first sentence of your post I'm going to guess that you're not toggling the playaudio key off when you're done playing a song (you have to hit it again to deactivate playback, even if the song has already stopped playing). If that's not it, then it's possible something else is keeping the file open preventing it from being overwritten, make sure no other applications are accessing voice_input.wav (again, I doubt it though).

[TooManyCats]

Nah, I have to stop playing the song. I press F1 to start it, the song ends, I press F1 to stop it, I load a new song, I press F1 to play the new song. Once to turn a song on, once to turn a song off, load a song, repeat.

[TooManyCats]

So, ahhh...

Any progress been made with this?

[Renegade]

somethings you might try:
- close HLDJ and delete any ".hldj" files you find in your Steam directory
- turn off Steam Cloud (in case it's trying to restore config files it shouldn't be)
- make sure you're using the latest HLDJ version
- re-download and re-install both the game and HLDJ
- test it on another game (always make sure to test on your own, unmodified server)

other than that I can't really say what it is.