As I suspected. This is a classic scenario that is occasionally seen anywhere: "everyone is underestimating a problem until a disaster strikes".
The team's perception of Tkinter is basically: "well, there are slight issues, and the docs are lacking, but no big deal."
Well, this _is_ a big deal. As in, "with 15+ years of experience, 5+ with Python, I failed to produce a working GUI in a week; no-one on the Net, regardless of experience, (including Terry) is ever sure how to do things right; every online tutorial says: "all the industry-standard and expected ways are broken/barred, we have to resort to ugly workarounds to accomplish just about anything"" big deal. This is anything but normal, and all the more shocking in Python where the opposite is the norm.
And now, a disaster striked. Not knowing this, I've relied on Tkinter with very much at stake (my income for the two following months, basically), and lost. If that's not a testament just how much damage Tkinter's current state actually does, I dunno what is.