I do something similar: passwords created by a script, stored in an encrypted file that's only unwrapped when I'm fetching or storing something. It's important

I do something similar: passwords created by a script, stored in an encrypted file that's only unwrapped when I'm fetching or storing something. It's important that the entire file is protected, requiring a password every single time. Like you, my biggest gripe is sites with special snowflake "make it hard to remember but keep it low entropy" password policies that preclude the original generated password. IMO we as a community need to start shunning such sites the same way we do for rogue SSL/TLS cert providers. As long as they exist, it's harder for even security-aware sites to move forward.