I’m thinking of ways to help people move from established software to more open, flexible forms that don’t lock them to another organization.
You would be surprised with how common it is for the lay person to have problems on their computer. I like to start from there, and suggest a free as in freedom software solution. Then, once their issue has been solved, I will talk about the free software movement, explaning that these are the reasons that have motivated the authors of the software solution I promoted. Hopefully this leads on to a discussion about freedom in the digital world.
For programmers, WSL with Ubuntu is a good starting point for those who are scared of Linux.
That is definitely not a good starting point. WSL is much more complicated and prone to breakage than running a distro directly. It litteraly changes the whole system to make Windows run on top of a hypervisor. A better way to try out GNU/Linux is to boot up a live environment on a USB stick or use a VM. Plus, WSL is only command line, and I would think that showing a friendly desktop environment is the best way to blow the assumption of GNU/Linux being hard/only for nerds.
