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> Making True == -1 looks interesting, but it has drawbacks.
Yes, please ignore that part of my post. :-) It shouldn't be considered seriously until a time machine turns up (and probably not even then).
My main worry with the proposed change is accidental breakage from the change in meaning. I've so far failed to find any examples of real-world functions that could/would be broken - the closest I've come is floating-point bit-pattern manipulation functions (constructing a bit-string from a sign, exponent and significand, where it's quite natural to treat the sign both as an "is_negative" boolean and as a 0-or-1 integer). But that case didn't involve a `~sign` at any point, so it doesn't count.
Still, I have a nagging suspicion that such a function will turn up if we make this change.
Having ~True *not* be the same as ~1 feels like a bigger surprise to me than having ~True not be False; it breaks my simple mental model that bools always behave like ints in numeric contexts.