"Maybe Clang/LLDB will help but it’s not clear how much they are focused on Windows either."
Doug, do you follow the LLVM Weekly newsletter?
I've been following it for half a year or so, and there seems to be an effort to make LLDB debugging work with the Visual Studio toolchain.
Note that LLDB on Windows means two things:
A) Debugging executables compiled/linked with Clang/GCC (DWARF debug info)
B) Debugging executables compiled/linked with Visual Studio (another format for debug info)
I haven't tried (A), but I assume it already works similar to Mingw-w64.
So (B) is the scenario they've been working on (and something that GDB will never support). They've made progress, but I'm not sure how far it is from actually being usable in an everyday case (it's definitely not ready yet - it takes time).
Scenario (B) would be very useful for developers who don't necessarily want to use the
Visual Studio IDE, but they have to because it's the only one that support the VS compiler toolchain - and they have to use that compiler toolchain if they use native Windows libraries like DirectX, etc.)