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)?
Yes
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_p.cfg
Loaded : Recording
4) After loading one of the sample audio files, perform a search of your Steam directory (without stopping HLDJ) for the file "voice_input.wav" - does it show up, and if so, where?
In the main Team Fortress directory. For me, that's D:/Steam/Steamapps/zackteach/team fortress 2
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 my mic works just fine.
The problem is something it seems like a few other people are posting about. The button I've bound for HLDJ is simply not playing any sounds. I thought maybe it was because my audio files weren't in the right type, so I converted them to both of the different types listed in the manual. Neither of those work though. All that happens when I hit F1 is my mic opens. It's not the server that I'm playing on, because many other players on this server make use of HLDJ as well, or alternate programs with the same purpose in mind. So I'm not sure what the issue is.
Playback button activates mic, not sound in TF2
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Re: Playback button activates mic, not sound in TF2
voice_input.wav is showing up in the correct place, try loading the sample audio files to make sure your audio is converted correctly. Also, test on your own server with sv_allow_voice_from_file set to 1.
Re: Playback button activates mic, not sound in TF2
Alrighty then, not sure how this makes sense, but maybe you can understand it better than me.
I tried creating my own server and testing the first sample audios from both Gold and source, and they had the same results. Then I thought, well maybe I should test all 6 of them just to be thorough. I created another server since I had already disconnected from my first one, and on that new server, all 6 of the sample files worked just fine. I made sure on the first server to set the voice_fileinput to 1, and I didn't even try to change that setting with the 2nd server.
My guess is that my files weren't quite the right frequency, although I thought I had it right. I guess that's just it though. Thanks for the help
I tried creating my own server and testing the first sample audios from both Gold and source, and they had the same results. Then I thought, well maybe I should test all 6 of them just to be thorough. I created another server since I had already disconnected from my first one, and on that new server, all 6 of the sample files worked just fine. I made sure on the first server to set the voice_fileinput to 1, and I didn't even try to change that setting with the 2nd server.
My guess is that my files weren't quite the right frequency, although I thought I had it right. I guess that's just it though. Thanks for the help

Re: Playback button activates mic, not sound in TF2
You can also try the HLDJ Audio Converter, which should always produce valid files.