Maybe half of these get chalked up to my ignorance! See picture at bottom for #1 and #2 (ignore the word "text")
I find that I regularly lose recently generated passwords. Yes, they're available in the "passwords" sidebar option, but they're not sorted in a way that I find useful. Easily finding the last generated password (or last 3?) would address my dumb mistakes (e.g. I go to manually update the login and press "copy" instead of "edit") and lose the generated password.
More and more websites permit only a small number of symbols in passwords (e.g. "you may only use +-/@$", etc.) Create an option within the password generator to do a regular expression search for, say, 5 special characters in a row on the current page. There's a pretty fair likelihood that those are the only permitted symbols. Then optionally restrict the generated password symbols to the sniffed ones.
A single password generated within Firefox for example.com is saved twice (once for Firefox, once for example.com) and reported as a duplicate. Since I'm striving to improve my security hygiene, this is an unwanted distraction that makes me falsely believe there's a problem.
The watchtower reports are great! To make it even better, optionally show weak passwords in date order. I'm much more concerned about recently used weak passwords than the throwaway password I created for some now defunct site years ago.
1Password Version: 7.2.4
Extension Version: 1.14
OS Version: OS X 10.14.3
Sync Type: Not Provided