I notice this forum is on the quiet side these days, probably terminally so given the developments with the company and their products.
Still, in case anyone else happens to read this, I have additional data points
I am all but certain the problem lies on the GV end, and in particular, the GV interface via the Obi 200 using the endorsed integration facility to link Obitalk directly to GV services, enabling direct dialing of GV on the analog handset.
As noted above, I have 2 separate GV numbers, and each one is given an SP location on my Obi200. The ONLY TIME call waiting does not work is when I dial out on EITHER NUMBER using the handset. If I dial on my primary number, and a new call comes in on the same number, it goes straight to VM. If I dial out on my secondary number and a new call comes in on that same number, straight to VM. However, if I dial out on one or the other, and the new call comes in on the opposite number, the call is allowed, and I get a call waiting tone and the number display.
Also, If I initiate the outgoing call on my browser using the callback feature, and then a new call comes in, call waiting works as normal.
The only constant factor here is using the Obi, with a handset, placing an outgoing call directly using the Obi/GV integration. Google Voice, when calling out from the handset, seems to "commandeer" that line, and any calls that come in to that number are sent straight to voice mail without even attempting to let me answer. But when using Google Voice thru the web app to initiate a call, it leaves the line open for incoming calls to answer manually.
Originally, Google Voice was not a physical line, only a virtual phone number which could forward calls to other numbers. You could not have natively dialed out on a GV line before. Now, it seems like GV has reverted to not playing nice with a physical hardware device occupying the GV phone number/line.
Unless, of course, there is some setting that I can change to enable the expected (and historically enabled) behavior. Which was my original question above.