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Output to two different Audio Devices at the same time

Is it possible to output PlayIt Live audio to two different audio devices at the same time?  I am using a product called VoiceMeeter Banana.  I am using its builtin "Insert Virtual ASIO" cable to send output from PlayIt Live to one of VoiceMeeter Banana's mixer hardware inputs (using the IN#2 Left/IN#2 Right portion of the cable).  I want to be able to send the PlayIt Live output to another one of VoiceMeeter Banana's hardware inputs.  VB Banana's "Insert Virtual ASIO" cable will let me do this by using the IN#3 Left/IN#3 Right portion of the cable.  But, I need to tell PlayIt Live to send it to both the IN#2 and the IN#3.  I thought I might be able to use Track Editing/Monitoring setting in PlayIt Live; but, it doesn't seem to work this way.  Is there a plugin that I could use to accomplish this?  Thank you.

I’m taking it that this is not possible?

Jeffrey, yes and no !

As far as I know, each "player" can only go to one device but if you have a suitable sound card it is possible to send two players to two different channel pairs and (say) the preview and cart players to a third. I have that setup working on a couple of systems.

The primary limitation is that PlayIt Live needs the sound device to present as multiple stereo channels.

If you have, say, a 5.1 or 7.1 channel sound card it can't currently map the channel players to the 5.1 (or 7.1) channels. 

Since this is an obvious and desirable enhancement my guess is that the limitation lies in the audio library that PlayIt Live uses.

Earlier versions of PlayIt Live could be used with ASIO4ALL which could overcome this limitation but as I understand it, ASIO4ALL caused more issues than it solved so is currently disabled.

If your "Virtual ASIO cable" can be made to expose multiple stereo pairs then you stand a chance. If IN#3 presents as a separate audio device try that with a different player.

Another limitation of PlayIt Live compared to, say Mixxx, is that you send the players to a device. With Mixxx the channel players and the composite mix are all available to send to devices.

While Mixxx and PlayIt Live suit different applications you could experiment with Mixxx and VoiceMeeter Banana and see if that will present on separate mixer channels.

I have tried Mixx before. I find it to be a very poor program that eventually makes audio output stutter and lag after using it for a half an hour or so even on a fairly powerful computer with really good audio components. Mixx lasted about two weeks on my system before I found another solution. That is where VM-Banana and PlayIt Software came in to play. They give me what Mixx promises without the lag and stuttering. Yes IN#3 Left/IN#3 Right do represent a separate stereo channel pairing on VM Banana. In other words I can send a stereo signal through the #2 L/R pair and a different stereo signal through the #3 L/R pair (or a duplicate of the signal going through the #2 L/R pair if I want, which is what I want actually). The #2 pair end up in hardware input 2’s stereo input in VoiceMeeter Banana and the #3 pair end up in hardware input 3’s stereo input. I have found a way to do what I want by installing and using an additional virtual cable to route hardware input 2’s output signal into the virtual cable and loop the virtual cable into hardware input 3. This accomplished what I was looking to do. I was hoping I could do it without introducing a third piece of software (the additional virtual cable). I hope that makes sense. If PlayIt Live could output the same clip to two different outputs at the same time then I could eliminate the virtual cable. You may be asking what I am attempting to do. I am trying to play clips from PlayIt Live both to an Internet destination and to my headset at the same time but have it play in my headset at a lower volume than it plays to the Internet destination without lowering the volume of other audio going playing in my headset. Having the audio from PlayIt Live meant for my headset going into a separate input on VoiceMeeter Banana, separate from all other audio sources, allows me to independently control the volume of the PlayIt Live audio for my headset from all other audio. Think of it as a live monitoring of the PlayIt Live audio for my headset that is at a lower volume than everything else playing in my headset.
I tried to do separate paragraphs for my reply above but for some reason the forum strung everything into one paragraph when it posted. I’m sorry about that. It makes the above reply difficult to read.

I'm not entirely clear what the headphone problem is, whether it is a balance against other sources of audio problem or just an absolute level issue. 

If the latter then some sort of sound card with a volume control should do it. You also seem to be getting towards the limits of what is easy to do with a "soft" mixer.

Have a read of this:

about what a "hardware" mixer can do.