Created attachment 465464 [details] emerge --info Attempting to get a mingw-w64 ruby build environment setup, failure on this dep.
Created attachment 465466 [details] emerge -pqv
Created attachment 465468 [details] environment
Created attachment 465470 [details] build.log
https://github.com/Alexpux/MINGW-packages/tree/master/mingw-w64-libyaml Applying the patches here allow for build.
you're using old versions of binutils & toolchain. your emerge info says you're using binutils 2.24 and gcc 4.9.2, neither of which we support anymore. upgrade to recent versions and see if the issue is still there.