Comment by Twey

It's a lovely idea, but so far all software personalization I can think of (in the sense of software adapting to the individual, rather than the individual adapting their software à la malleable software) has been weaponized against the user rather than used to support them. Occasional attempts in the other direction like adaptive user interfaces (https://en.wikipedia.org/wiki/Adaptive_user_interface) tend to fail because they break habit formation (c.f. Raskin)