IDK, I think the idea of a mega-polygon (Carmack, is that you? ) is kind of interesting, though, it seems like if you had a lot of onscreen shadowcasters the complexity of the polygon might become a problem.
However, the light/shadow system was quite a bit of work, and I'd be surprised if Ashley didn't try something like this along the way, as I've read about other implements before that did something similar to what you are suggesting.
I suspect this would gobble up a lot more fill rate as well, since rendering the 'inside' means overdrawing substantially more pixels. Which is a problem for perf on desktop, unless you want to ignore the massive number of people rocking iGPU's only (wish we could, but... ).
Anyway, I'm going to shut up now, because I'm starting to get way out of my depth...