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Turns out there are major drawbacks in the previous change.
Let that be a warning to the next person that is trying to simplify things in the JS world in the current times: DON'T!
TSC doesn't "support" having extension-less imports when compiling a module, they refuse to make the right links, this only works with commonjs. Jest in the other hand doesn't fully support this approach so we'll have to keep building files before testing or try some experimental solutions meanwhile.
IMHO ideally we should stick to basic commonjs modules and wait until the ecosystem is more developed towards modules. Reverting to commonjs may not be worth the trouble right now so we just keep things going as they are.