And Hanselman works for Microsoft, where i18n is a big deal. So yes, for someone who's been at MS for a while i18n related issues become second nature. But if you typically are only targeting the United States, it's more understandable to not have these things on the brain.
On the other hand, Outlook still has a ridiculous bug that uses the wrong encoding when presenting HTML email - that is, it uses the encoding of the email's text-body when presenting the html-body, even if the html-body specifies a different encoding.
So, if the two bodies have differing encodings (charsets), then the HTML body will look wrong. Unless you force Outlook to always use UTF-8 for encoding emails (which is a setting, but not the default) then you'll end up sending emails that will look garbled to your recipient.
This "differing charset" scenario actually happens pretty frequently, because of the following scenario:
a) You write an email (or reply to an existing email - actually it happens most with replies).
b) Outlook's text editor decides to insert a non-breaking space (codepoint U+00A0). Perhaps it generates HTML with but before transmission this eventually turns into the single UTF-8 character 0xC2 0xA0.
c) When generating the text-body, Outlook decides to just use a plain old space, so the text body is plain ASCII.
d) Outlook, in its cleverness, then says "ooh, I can 'conserve' encoding-ness and use plain old iso-8859-1 for the text body, but I need to use UTF-8 for the HTML body because of that non-ascii character"
e) Outlook generates this email (please excuse formatting woes due to HN).
You should file this at connect.microsoft.com. MS devs and PMs really do read and triage bug reports coming from there. The more details you put in the bug report, the better.