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 How do you think we could better facilitate and teach users about self hosting? This is the only real privacy option, but the barrier to entry is so damn high for most users... 
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 I don't think it is, not anymore.
I think the main barrier to entry at this point in time, is the misconception of necessary effort.

If we present it as a step-by-step what needs to be done, they may say it's too hard or too much. 
If we present it as an afternoon-project, they may be more open to it.

That being said, in general, people are lazy even when it comes to their own welfare in the privacy context, but I think there's something in how it's framed that's worth exploiting. 

As an example, you can spin your own full-fledged cloud service in a couple hours at this point in time:
- Get some hardware (raspi (or similar), old laptop, PC etc)
- Change a couple lines in a docker-compose file
- Run a single command
- Final Setup via the webpage

Based on the four steps above, if someone can't spend a half hour understand each of those steps, then I can't say they actually WANT to protect themselves.

You also have all-in-one setups like Start9OS that allow you to then install the apps via a marketplace. 
 I think you need guided setup like umbrel. 
 Isn't Umbrel essentially just an app store that runs everything via containers?