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JavaScript (Node.js), 147 bytes f=(a,b='IVXLCDM',g=Math.log10(a)<<1,c=10**(g/2),e=a/c|0,i=b[g+1],j=a=>b[g].repeat(a))=>a?(e<4?j(e):e<6?j(5-e)+i:e<9?i+j(e-5):j(1)+b[g+2])+f(a...
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# [JavaScript (Node.js)], 147 bytes <!-- language-all: lang-javascript --> f=(a,b='IVXLCDM',g=Math.log10(a)<<1,c=10**(g/2),e=a/c|0,i=b[g+1],j=a=>b[g].repeat(a))=>a?(e<4?j(e):e<6?j(5-e)+i:e<9?i+j(e-5):j(1)+b[g+2])+f(a%c):'' [Try it online!][TIO-kiam9mmx] [JavaScript (Node.js)]: https://nodejs.org [TIO-kiam9mmx]: https://tio.run/##bY5Bb4JAEIXv/g/DjrvorkECyMihvTSpV9Ok4TCuA0KMGCWe@t/p2mMztzdf3rz3enrSw9@72xhfhxNPU4OKzBGjj8PX59v7PjIt7mk8Ly9D66wiKEtnPDq7WKh2tQbDSCv/Y02Hx@9Wu9r0SLgLul7e@cY0hh/AHVWKy6TqFUPBZRrEJmbQXTjyqtOBxxsoeuVAv3LWNehG0dxDEUXT1g/Xx3Dh1wjVBA9sZ/9YJrBcYM4KMEkEmKap1GOlgCwT@0Vvnsu7/szTLw "JavaScript (Node.js) – Try It Online"