I suspect there is some other problem relating to copy/paste from Word vs. the em-dash itself. I frequently use em-dash using just the character and have never had a problem. An alternative approach to get an em-dash during conversion though is to use double hyphens -- and enable 'smarten punctuation' during conversion.
I'm not sure if you solved your issue around blockquotes - this is something else I use all the time so not sure why you're having a problem here. Posting your conversion settings and perhaps a snippet of the source code could help.
If your formatting requirements are relatively simple (by the screenshots they look like they are) you can try using text with Markdown or Textile instead of whatever combination of Word/HTML you're using. Those are my preferred formats if I'm starting something from scratch or really poorly formatted text.
Here's an example using only markdown, smarten punctuation, and extra css - '>' creates blockquotes:
Code:
PART I
-------
### THE MESSAGE
>My heart trembles like a poor leaf.
>
>The planets whirl in my dreams.
>
>The stars press against my window.
>
>I rotate in my sleep.
>
>My bed is a warm planet.
>
>>--M<span class="smcps">ARVIN</span> M<span class="smcps">ERCER</span>
>>
>>P.S. 153, Fifth Grade, Harlem
>>
>>New York City, N.Y. (1981)
Extra CSS:
Code:
body{font-family: serif}
p {margin-top: 0em; margin-bottom: 0.3em; text-align:justify}
blockquote {margin-bottom: 0.5em; margin-top: 0.3em}
p + blockquote {margin-top: 1em; margin-bottom: 1em; margin-left:15%}
span.smcps { white-space: pre; font-size: 80%}
h2 {text-align: right; margin-bottom: 0em}
h2 + h3 {text-align: right; font-size: 2.5em; margin-top: 0em}
blockquote > blockquote {padding-left: 20%}
