With regard to the whole self-hosting thing, perhaps it is worth copying the way Rust handles this:

https://github.com/rust-lang/rust/wiki/Note-compiler-snapshots

So in order to build one would usually download a binary compiler and use it to bootstrap, but in theory one can take the last version of the compiler before it became self-hosting, and build all the way to the current version (but it would take a long time).

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