So I'll handle this in two parts. But I want to preface everything I say with I don't really know enough about the compiler toolchains, everything I say is from anecdotal experience of myself and what I've heard from others.
The first part is understanding that the Devkit is actually two parts, The first part is msys and the piecemeal tools that we need during the compile process, then the other part in mingw itself.
So to replace the compiler you would just need to make a new file/entry in the compilers folder.
So, here is why the DevKit isn't updated lightly. The `--platform=ruby` tag is basically saying, "Hey, give me the code I'll compile it all myself." Meaning you'll handle all the dependency management, and the compiler chain management.
Which brings us to... The compiler toolchains are interchangeable, except when they're not. I don't know enough to know when they are or aren't.
Also there are a couple of different libraries and tools that facilitate the ability for gem creators and maintainers to create versions of the gem compiled for Windows machines. They're all using the same version of the compiler toolchain(mingw) so we won't have weird segfaults. So it's kind of an ordeal to update it.
So, if you were to build your own Ruby using your own DevKit I would recommend ONLY using `--platform=ruby` if you want to be certain of no segfaults, but it means you need to handle all the library stuff yourself.
There's a lot more to it, but that's a quick gist of the DevKit and the problems, including my gaps in understanding, that have prevented me from upgrading the DevKit plus some info on how/when to use your own.
I kinda forgot what it was like to not be looking at this stuff and know what it is/does so feel free to ask more questions if I failed to explain it well.
Justin