Any reason not to redirect entire directory from old site structure to new?

[wattssw]

I'm helping on a site that has tons of content and recently moved from a 10 year old .ASP structure to WordPress. There are ~800 404s, with 99% of them in the same directory that is no longer used at all. The old URL structures offer no indication of what the old page contents was.

So, there is basically no way to manually redirect page by page to the new site at this point.....is there any reason not to redirect that entire old directory to the new homepage?

Matt Cutts seems to think its OK to point an entire old directory to a new homepage, but its not as good as the 1:1 redirects: http://support.google.com/webmasters/bin/answer.py?hl=en&answer=93633

Any thoughts?

[cbielich]

Well think about it like this. Would you rather have a ton of 404's linked to your site? or would you rather risk the PA on each of those pages and redirect them to 1?

If you decide to not redirect to a single page then at least remove the urls in webmaster tools so you can seem a little better to google

[wattssw]

That's how I see it....the old homepage was at ..../af/index.asp -- this will definitely get 301ed, its just about the other 800+ random URLs.

There is no penalty for redirecting a page that could otherwise have a 404? Or, once GoogleBot views a 404 on a particular page, is it too late at that point to 301 it? With the "index.asp" page, it still makes sense to redirect because there are links around the web pointing to that location, and those visitors need the redirect.