Hello again @IM00IR thanks for letting us know you've run into these issues.
1) I can see there is an issue open with the development team looking into resolving a related issue. While I certainly understand it's not an ideal workaround, when editing the item to reset the password, you can copy it into the second field. My apologies for any trouble here.
2) I think this is an interesting idea. In situations like you described could you switch to a random password to set a specific character count or do you prefer to stick with memorable whenever possible? With memorable passwords have you found that some passwords within the same word length work and other don't?
ref: dev/core/core#16684