Great writeup and a fantastic usage of @r2gui! 
Haven't looked at the binary yet, but I wonder if it is possible to retrieve the flag using Cutter's emulation. Did you try?
just published my blog on solving the vm1 challenge by @MalwareTechBlog using cutter (@r2gui) for beginners
https://daringjoker.wordpress.com/2019/11/26/malwaretech-vm/ …
@radareorg @maskop9
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i haven't tried it since the goal was to do the static analysis and i don't think the ram content is loaded to vm at any point but i will definitely give it a try.
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