As a technically lay person who does care about this, what are some tools that I can use to write web copy with typographically correct apostrophes and quotes (or convert it afterwards)? Am I supposed to use the html code or special key combination every time?

If you're on the Mac:

    “ = Alt-[
    ” = Alt-Shift-[
    « = Alt-\
    » = Alt-Shift-\
    ‘ = Alt-]
    ’ = Alt-Shift-]
    — = Alt--

For other operating systems there are typographic layouts, such as http://ilyabirman.ru/english/typography-layout/

There are libraries that can do the conversion, such as SmartyPants: http://daringfireball.net/projects/smartypants/

In HTML, it's pretty easy to remember a few typographic characters that you'll need, see http://www.degraeve.com/reference/specialcharacters.php

Thanks for those suggestions. So, then, do you (or others) actually use those key combinations instead of ' and " while writing/typing? That seems like a fairly heavy re-working of a very low level muscle-memory process that would take me a long time to habit-change.

I don't use any of the software that Smartypants supports, but I just started playing with Pandoc http://johnmacfarlane.net/pandoc/ yesterday, and it has a --smart flag, so that's probably what I'll go with.

As I also recently started trying to learn vim (it's hard), I might try this: http://www.oreillynet.com/xml/blog/2005/10/smart_quotes_and_... too.

In case anyone else is in a similar position.

For my blogs, etc. I just process everything via Textile/SmartyPants/similar.

For other writing, I don't bother to insert proper quote marks, but usually use a proper dash.

BTW, Mac OS X since 10.6 can automatically replace quotes in any Cocoa textview, but I have it turned off.

The problem with "smart typography" is that is must be language-aware: quotes used in «Russian» are different from “English” and „German“ and »other« »styles»: http://en.wikipedia.org/wiki/Non-English_usage_of_quotation_...

  As a technically lay person who does care about this, 
  what are some tools that I can use to write web copy 
  with typographically correct apostrophes and quotes

I use Textpattern CMS, which has built-in support for Textile (they were built by the same developer.) Textile converts marked-up text input to valid, well-formed XHTML and also inserts character entity references for apostrophes, opening and closing single and double quotation marks, ellipses and em dashes.

http://textpattern.com/