adder - 9:56 am on Nov 16, 2012 (gmt 0)

So, I'm in the process of rebuilding a large news section with an enormous amount of inherited problems. I've decided to make the urls nicer (this will also sort out a weird duplicate content issue).

It means several thousands of 301s. I spoke to this chap and he recalled a classified site having been dinged for introducing too many 301s. No-one can remember what site this was, so I cannot verify :)

1. Have you ever heard of a site that has suffered from having too many 301s? And I'm not talking about cases where 301 was implemented awkwardly. There are many ways you can get this wrong technically, but let's assume I do everything properly, i.e. old/ugly/article/url redirects to /new-and-shiny-url

2. Many of the articles are mighty old but I still want to keep them. If I change the urls now, when Google finds out the article resides on a new url, will it update its index or will it simply drop the old article? I've noticed that sometimes Google cannot be bothered re-indexing old articles but this was on a small and non-authoritative site.

3. A bit off-topic. If some of your news articles linked out to a relevant product page, considering the article was good quality and it really spoke about that particular product. Would you say this is a problem? Does that look spammy? From the visitor's perspective, there's nothing wrong linking to the Blue Widgets sales page from a news piece that speaks about a brand-new version of a Blue Widget. But since the ultimate goal is becoming an approved Google News source, I might reconsider what I do with links. What do you think?