It's only a pain if you're still trying to use PGP. You can download Inky (http://inky.com) for any platform and use any email account to exchange S/MIME-encrypted email simply by checking a button. We're focused on large enterprises now (because we've found consumers and small business don't care about encrypting their email, or think TLS=encryption) but there's nothing stopping individuals from trying it out. It makes e2e encryption of email using any email account basically invisible. You can send encrypted mail to non-Inky users as well.