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I would love to read the story of someone who walked from Siberia to Alaska via the shortest sea crossing possible. But above Magadan, there are no more roads. And the Kolyma highway to Magadan is considered a major adventure already, with only a small window where the rivers are low enough to be crossed by motorcycle (and therefore, man).
I'm not saying this can't be done, but it looks like a serious arctic expedition to me. Which I kind of doubt he will do. This is probably going to end like usual. Helpful Russian truck drivers take him with them for as far as they can go, then (Mommy!!) a helicopter shows up...
It seems like there's a gap between small one-off jobs that are posted on Upwork, and projects that require multiple full-time engineers. RemoteHacker seems to sit perfectly in between those two options.