Once a chip architecture gets popular on Windows, it will be hard to displace. ARM has already become popular on macOS ( via Apple Silicon ) so we know that is not going anywhere. If ARM becomes popular on Windows ( perhaps via X Elite ), it will be hard to displace as the more popular option. That makes RISC-V on Windows a more difficult proposition.
I do not think that RISC-V on Linux has the same obstacles other than that most hardware will be manufactured for Windows or Mac and will use the chips popular with those operating systems.