If you use mismatched versions of Outlook and Word, and you've chosen Word as
your email editor and send an email with an attachment to a non-Outlook user,
you may find your attachments are stripped from the email.
Regarding Outlook being reinstalled every 6 months, you need to provide more
information such as Outlook version, Windows version, error messages,
symptoms, etc. Also, is your system fully patched (Windows Update and Office
Update), your antivirus up-to-date and your system scanned regularly, do you
run antispyware applications such as Lavasoft, Spybot S&D, and Microsoft
antispyware? Are these applications kept up-to-date and your system scanned
regularly?