Assuming you mean “Can I upload files from within Dreamweaver instead of using a regular FTP/SFTP client”, the answer is yes, as long as DW supports regular FTP/SFTP.
Dreamhost, for reasons unknown, does not provide SMTP over SSL/TLS. You can, however, use SSL for POP3, IMAP, or webmail. If you’re concerned about password security (as you should be), I recommend sending mail via your ISP if they offer SMTP over SSL/TLS or don’t require SMTP AUTH at all. That’s what I do. If you’re looking for security for the entirety of your message, no one can give you that. Look into PGP.
If you want useful replies, ask smart questions.