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This is such a nuanced question that depends on so many different factors, I fear I can't give you a complete answer. But I can tell you some of the questions I'm asking in my head. -What happened to the old para-sailing pages on Site B? Do they redirect to the salespage/homepage? Does the site still rank for and receive traffic for para-saling? What did those old pages rank for? -Are you trying to rank the new site for para-sailing queries? If so, it might seem appropriate to redirect the old para-sailing pages to the next most relevant landing page. This is what Google would prefer, anyway. -Do you take up 2 SERP positions now? That's off the top of my head. Would probably have some more questions if I saw the site and knew more about the particular queries.

If your rankings are good then I would leave it as it is.. put it on the list of future plans and then change it if you do some major dev work that requires you to change urls

I haven't seen any evidence that it's a problem, but John's point is correct - Bing does officially say not to do it. Actually, Google originally said this, too, but then eased off (if I recall correctly). It's gotten so common that I don't think either engine can really penalize it, honestly. I do it all the time.

Just change the keyword at the end of this URL: wordpress.com/tag/cakes/ You'll also see related tags to the right.

Thanks John.