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If you were using either Compressor plug-in built into Ableton, you would be able to select your Drum track in the "Sidechain" panel of the compressor, accessed by pressing the little arrow in the top bar of the plugin. You don't need to use the "Audio to" function at all. I wouldn't be surprised if your VST Compressor has a similar function.
Basically ...
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If your other MIDI receiver is hardware or software running on another machine, you simply route the midi track to a midi output (granted that your interface has a MIDI out port).
On the other hand, if you need to route the output to some other software on the same machine, you need some virtual MIDI port (or "loop back") software. One solution is loopMIDI:
...
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It is an amplified headphone distributor. Sweetwater.com has many. There is a cheap one for $30 but most are a $200-300 and up. If you get an inexpensive one, make sure it’s powered - otherwise it can only lower outputs to match the most efficient (loudest) headphones being used.
If you are mixing on headphones, you will be at the mercy of the quality of ...
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Let's assume it's a problem with audio signal flow within Cubase (the version I'm going off of is Cubase 7 or 8 Pro):
In Devices > Device Setup..., under VST Audio System, make sure that your device driver is the one selected in the dropdown menu at the top of the window.
In the same menu, click on your device name in the list under VST Audio System and ...
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To make sure you've got the USB interface set to 32 channels:
Setup menu, Card tab:
set to 32 in/32 out.
To connect the USB input to the 32 channels:
Routing menu->Home tab:
this is a list of possible inputs that can be assigned to the channels. This is done in blocks of 8:
In the input 1-8 column, select the row 'Card 1-8'. This assigns channel 1-8 of ...
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Have you considered using Dante Via to achieve connectivity between the computers?
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ASIO bypasses the Windows audio interface to connect the DAW straight to the sound card; so selecting that as your audio system will not allow you to bypass and use it at the same time. You can try to set it to WASAPI and see. I don’t use Reaper though.
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Hmm. Not sure you can do this under windows. With OSX it would be easy as you would create an "aggregate" device which includes both of these two hardware options and then you can route directly from reaper through the aggregate device to the required hardware output.
Unless Windows has the option of creating a 'virtual' or 'aggregate' device, I fear you ...
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You might look into Soundflower for an Apple solution. There are tutorials online - that is just one example. Loopback might be a newer solution, and I believe there are tutorials for that as well.
JACK and VB-Audio CABLE were already mentioned and are popular for other platforms.
To do fancier things, have a look at some of the Source Elements remote ...
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As far as my knowledge go, this would be the "right" setup for you:
IN FRONT OF THE AMP
Guitar --> Wah (you did not mention it, but it needs to be first in line, because wah, along with fuzz, is "tone sucking", and putting them last in line would not be good, since the signal has already been deteriorated passing trough lots of pedals) --> volume --> tuner ...
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