I finally got bored enough to crack this puzzle. I knew it should work but just wasn't patient enough to get it all sorted out. The goal here is to use virtual audio from your PC via the USB port into the 590 in order to transmit that audio over SSB or AM or whatever.
The reason for doing this is that I have a common microphone that is connected by a Motu M2 USB pre-amp interface to my PC that I then process using Voicemeeter as a mixer and Reaper (similar to Cakewalk, Pro-tools, Studio One etc) as the processing/DAW to do things like EQ, compression, de-esser, multi-band comp and stream clipping for loudness.
I would put this into the bucket of something to do if you are sufficiently obsessive over your audio, patient enough to deal with the complexity and ultimately, bored enough to sink time into this.
Some basic bullet points.
Rig has to be in DATA mode to allow the audio through, so LSB or USB, but in DATA mode.
Menu 70 , source of send/PTT must be set to rEAr
Menus 71 and 72 are your microphone input gain level and the output audio level
Menu 69 Input Line Selection for data communications needs to be set to USB.
Menus 33 and 34 determine your TX bandwidth in DATA mode
Menu 29 data filter should be in mode 1 so you have the right hi/lo pass for voice SSB
Ok so all of that is set up. If you've never used your 590 for digi mode use, you'll want to go into the sound control panel in Windows or whatever OS you are using and locate the USB Codec device for the 590. There's a Playback device and a Recording device. The Playback device I renamed to TS-590sg Input drive and the Recording device I renamed to TS-590sg Waterfall Level.
You'll want to find a balance (I'd say start at 50 for level on both) between those levels and the Menus 71 and 72 in the rig.
In order to PTT the rig to pass audio over USB, you MUST use the Send key, the Send key in the ARCP-590 software or, wire a 13pin DIN to the ACC2 port and use pins 9 PTT and 8 GND. It is important that you use pins 8 and 9. If you key with the other options for PTT or via the mic jack, it will all mute the USB audio.
Now to the audio puzzle.
My microphone comes in via a USB pre-amp box, a Motu M2 (others also work just fine). It is seen as an ASIO input device.
I "attach" the input device of my microphone to an input on Voicemeeter Potato, which is a software audio router/mixer. So input one on Voicemeeter is assigned to my Motu M2's Input 1.
The Kenwood audio codec is assigned in two places on Voicemeeter. One as an input source so I get the receive audio going into Voicemeeter. The other is as an output device so my mic audio will get sent to the Kenwood. In my case I assign the Kenwood as device A5 for the output bus.
In Voicemeeter channel 1 is the mic input and I click the "A5" button there to send the mic audio to the Kenwood.
In my Voicemeeter, I assigned channel 5 as the RX audio coming out of the 590 and I just click "A1" to send it to my main soundcard output to hear the receive audio.
Deeper down the rabbit hole, in Voicemeeter system settings I have inputs 1 and 2 set up as audio patch so I can send audio out to the Reaper DAW for processing and have the result come back to the input channel strip.
The tl;dr of the audio routing
Mic into input one of the Motu M2 -> USB to my PC as an ASIO sound device -> Voicemeeter software uses that as an input device -> Voicemeeter then sends the output of that to my Kenwood.
Kenwood RX audio -> USB -> PC -> Voicemeeter as an input device -> Voicemeeter routes to whatever sound card I want to listen on.
Why do this?
You bypass the pre-amp in the mic jack, so you gain some dynamic range, the audio just sounds a bit more "open" and clean.
You can used this processed audio for your 590, for making Skype or other conference calls or with SDR rigs that support VAC audio (I have two). So in my case I have one mic, with one unified setup to use for three rigs and whatever other PC based things I want to use it with.
Though it has a learning curve and headaches of its own, there is simply no more powerful or less expensive way to process audio than doing it in a DAW. Even paying for licenses I didn't have to, I'm in for maybe $150 for capability that would be several thousand in external rack gear.
Don't forget that the ARCP-590 software from Kenwood has the ability for you to really tailor your audio via the User EQ settings in its DSP tab. You can also set the User RX EQ as well.
*** The front panel mic will still work at the same time. If you toggle DATA mode on, it uses the audio from the USB, if you turn off DATA it will go back to the front mic jack, either audio path is disabled when toggled in or out of DATA mode. Also DATA mode will work in AM as well.
The combination of all of this is that you potentially get the absolute best audio the TS-590sg is capable of.