I like this idea.
However, there is a problem with punctuation and capitalization.
C++ Beginner - Trouble using classes inside of classes
would probably end up looking like
c beginner trouble using classes inside of classes
Which, as you can see, kind of changes what the question is about (C++ to c). This would be a problem unless you were committing to do a DB lookup every time a link is typed in/submitted in a comment or answer, in order to the get the correctly cased and punctuated title. Those lookups may add up (look at how many links I used in this post alone, so isn't necessarily a good idea in terms of performance. Although, Jeff might just want to throw some hardware at it.
All links of the format
"http://[((meta.)?stackoverflow|superuser|serverfault).com/questions/[\d]/ < QuestionTitle>"
(Could somebody fix my regex, I'm rusty)
would automatically be converted to
Or, if the question title is too long
vb net how to require checkedlistbox... or VB.NET: how to require CheckedListBo...
This would only be done once, at the time that the comment or question is initially linked. If the title of the question changes, the comment text would not change, because the link itself has not changed.
This magical replacement does not apply to people who are linking directly to answers, edit pages, or specific revisions. It could theoretically work for user pages, or tag pages.
A second alternate implementation would be to green jagged underline the link (like a grammar error), and have a rollover click option that says "convert to title hyperlink" or some such text. This would do the conversion that I described earlier, except that it would be optional. Further, because it would be replacing the text before the user has submitted the comment, it shows them how to do linking correctly (which they might not now) and it gives them the chance to change how it will appear. This is almost ALWAYS better than any "autocorrect" options. I hate autocorrect.
The (rather large) downside is that this would be more difficult to implement than a straight Regex replace.