Simply Linux 10.2

Significant challenges to get Debian v2 userspace running in that scenario:

    You'd need to manually install an old glibc, libc6 and other core libraries suited for Debian v2 without being able to leverage Debian's packaging system. Difficult to make it a consistent environment.
    Binaries built for old architectures like i386 would not run on x86_64 without emulation. You'd have to rebuild or source old binaries.
    Essential daemon processes like init, cron, syslog etc would need to be recreated or backported to run without the old kernel APIs.
    Network configuration and interfaces would be mismatched with the Docker host networking. Lots of tweaking needed.
    Filesystem layout, devices, mount points would not align with what an old Debian distro expects. Manual configuration is prone to mistakes.
    Old config files would need to be adapted for the containerized environment. Running commands could behave differently.
    No apt or dpkg for package management - everything would have to be installed manually. Difficult dependency resolution.

Overall, starting from FROM scratch eliminates one hurdle but all other challenges remain. I would still consider this an impractical undertaking compared to starting with a compatible modern base image. The amount of tinkering needed to recreate the userspace would be extremely tedious and error-prone.

Older Linux distributions like Debian v2 were built for 32-bit x86 processors (also known as i386 architecture). Programs compiled for those old 32-bit systems won't naturally run on modern 64-bit x86_64 processors without some additional steps.

There are a couple options to get 32-bit i386 binaries running on a 64-bit x86_64 host:

    Recompile the source code on the 64-bit system to build a new 64-bit binary. But this requires access to the old source code.
    Use an emulation/compatibility layer like qemu-user or binfmt_misc in the kernel to emulate an i386 CPU. This allows running the old 32-bit binary unmodified. However, there is some performance overhead.
    Run the 32-bit binary in a 32-bit Docker container on the 64-bit host using multi-architecture images. The container then acts as the emulated i386 environment.

So for an old Debian v2 userspace on a modern system, any proprietary binaries or programs you don't have the source for would need to be run under emulation. Or you'd need to recompile from source if available to build a 64-bit version.

Trying to run those old i386 binaries natively on x86_64 without emulation would result in errors as the CPU instructions are incompatible. Let me know if this helps explain the challenge!