To tie this back to Wine, here is what we actually do during some parts of the Proton[1] build process: Run a Debian 9 VM, inside of which we run an Ubuntu 12.04 Docker container (the Steam runtime), which runs an Arch Linux chroot in order to gain a modern cross-compiler. It's a doozy[2]!

[1] Proton is Valve's fork of Wine which ships with the Linux Steam client.

[2] https://github.com/ValveSoftware/Proton/commit/d68e71bed61c8...