Then you are forced to start fiddling, and this is already doom, because you are supposed to be getting stuff done, not fiddling. But at some point you become seduced by this vision of having a hyperoptimized, automated system in elisp and plain text that practically runs your life for you and frees you from having to make any decisions, frees you to think about important things. Except, the opposite happens.

This reminds me strongly of why I stopped using Gnus/Mutt for email and simply settled for Gmail. Customizability & power can be a dangerous temptation into endless yak-shaving. Even if you explicitly remember that customization need to pay off and calculate it will work out (https://xkcd.com/1205/), you probably overestimate how long you will use a particular system and underestimate how much work it will be to get it fully debugged & reliable.