As I didn't get many (any) replies I thought I'd just post to myself. Is that the 21th century version of a crazy man talking to himself??
I did finally make this work, just not by using VoiceAttack (save for automating the commands I give V (that's the VR overlay app). As it's hardcoded to use an Xbox controller I couldn't use any of the simple controller emulators out there - save for one.
I used an app called vJoy which then has a feeder (sorta like a plugin) to emulate a "real" Xbox controller. What I mean is when you look at your joystick devices rather than seeing something like Generic Joystick you see "Controller (XBOX 360 for Windows" which is what V is coded to use. So here's the workflow
JoyToKey binds specific keys to a specific joystick input (button, hat, trigger, etc). Then vJoy detects that keypress which is then mapped to a specific item on the virtual Xbpx controller. Once that's done and the app is started and running Windows thinks I just plugged in a controller. I then launch V while inside VR (notably Elite for me) and bingo, I can use my hats and a few buttons to then control V. I bound the mouse in V to one of the analog hats so I can even move the mouse to click on things inside V.
Quite a few steps but really not that hard. I already use JoyToKey extensively and as such knew what I needed to do there, it was just the "real" controller emulation that I needed to work out.
Just in case another wants to do this someday there you go, that's how I was able to make it work - and work well.
~X