I have an old website that hasn't gotten much love over the years and that's about to change. The existing site is based on a 3.* version of an ASP.NET portal framework called DotNetNuke (DNN).
I'm going to pull that site down and bring up a new site based on a static site generator called Nanoc (Ruby based). I'll be serving the site with nginx.
I'm not sure how to go about redirecting the old pages on the new site. Many of the new pages will be completely new; several of the old pages will not be back up. I suspect there will be a few that I'll want to keep alive in some form, but certainly not with the same urls.
Should I be concerned with doing a fine grained redirect on each of the pages on the site (it's not a large site), or just handle it with a general redirect?
You only need to bother with 301's (permanent redirect, better than 302) on links you want search engines to know changed, or if people might have them bookmarked. Other than that, I would just redirect 404's that look like an old URL to your new home page.