I'm doing a test run with some folks in my group tomorrow to get our voice chat setup squared away. One thing I really like is using music in my games, but I don't want to just run it on the speakers in the background. Is anyone aware of an app or program that would allow one to play music directly through the voice chat (or maybe as a separate connection)?

If it matters, I have at my disposal a Windows 7 laptop, an older iPad (1st or 2nd Gen), and a newer Android phone. One buddy has an iPhone, iPad and a Mac laptop. My general plan is to use Google Hangouts, though not with the Roll20 EotE tools (apparently I'm old now, as I don't understand it for squat and I don't care to learn. Lemme go plant some lawn for you to get off of). I'm open to other voice programs, but I want to be able to share pictures and whatnot easily enough.

Were I to do this on my mac, I'd use Soundflower - however, I'd be concerned about the bandwidth usage and having it interfere with the ongoing chat. To address those concerns, I'd look at the modern equivalents of internet radio and set up a limited broadcast . Still, I would cast a wary eye on doing this since video chat tends to be pretty hungry.

Any program you use other than Roll20 will probably have an even more difficult learning curve and won't have the benefit of native integration. Roll20 + Google Hangouts gives you access to SoundCloud AND Tabletop RPG music, all in the same interface.

Here's a playlist of 3 short clips that demonstrate what you can do with Roll20 and Google Hangouts

Roll20 + Google Hangouts gives you access to SoundCloud AND Tabletop RPG music, all in the same interface.

This is a great solution unless you want to use music protected by copyright, like the soundtracks. Soundcloud won't let you share a private playlist with Roll20, and with a free account you're limited on the amount you can upload. Can't disagree that this is probably the easiest solution if one is not constrained by those caveats, though!

I use the soundtracks pretty heavily in my game, and it's been on my mind to find a reasonable solution for transitioning to a virtual tabletop.