A modern password manager (e.g. 1Password) seems like a way more natural solution that this. Not to mention that many services do not use smtpd+ssl/tls.
To your second point. Yes, this is true. But this is improving [1]. I'd add that forgot password functionality carries the same risk, and I'd add that the more likely chance of your password being 'discovered' is by brute force or a website hack storing passwords in plain text - rather than intercepting email.
[1] https://sendgrid.com/blog/sendgrid-and-the-future-of-email-s... (I work at SendGrid)
How about Apple's Keychain? iOS and Mac users get suggested auto-generated passwords that are then automatically saved and synced across devices with no extra installs or options.