I think we need idealism matched with pragmatism to some degree. The example thread of someone with a story about Stallman going off on noise cancelling headphones is a good example of what I'm talking about. While he's technically correct that sort of misses the forest for the trees I think and turns people off. Stuff like LibreJS is a good example of this too. I understand the intent and again it makes a good point how many people use it?
Devices are becoming ever more complicated and requiring firmware for basic functionality. The FSF being picky about certifying distros due to including non-free firmware is something I wish they would back off on a little. It's not ideal but I think the approach they have now is letting perfect get in the way of good. Fedora and Debian are not perfectly free, but compared to Windows and macOS they are much better. For most people a computer is a tool and needs to get a job done if the options they offer people don't work on most machines or situations then it stops the conversation right there. Basically if you open with "well, you're going to need a new laptop with XYZ and learn to live without WiFi to be truly free" instead of just "lets put Fedora or Debian or Mint on this thing and get you excited about free software" it kills it out the gate IMO. Switching platforms is a daunting task in and of itself, let people think about one thing at a time. If we can grow theuser base and they start asking for more free software in their distro that might nudge the needle a little instead of just building our own fort.
Focus on the things free software does well vs non-free proprietary solutions. You control your machine again, DRM free means no one can take your media away, etc.
Most things are done in the cloud today and that's not going to change. I like that GNU started federated social media with GNU social but they've kind of let that rot on the vine. Same with MediaGoblin. I know FSF lists Nextcloud in their directory but it's kind of buried. That's the stuff people need/want these days. Maybe start working with approved Nextcloud hosts or setup their own instance for people to use for $X per month. Getting people off MS and Google be it on the desktop or in the cloud is a good goal.
For the mobile space I don't really have a good idea.