Dynamic to Static back to Dynamic?
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every 301 in a sequence of changes slightly degrades value. Do that three, four or more times within a year, across many pages, and you're begging for trouble. At a certain point Google's system will become so confused your site will surely suffer.
Part of the reason is their algorithms make decisions both based on evaluating an individual page as well as how their system interprets how pages relate to each other - including what links exist to a specific URL. That includes both internal linking and inbound linking from other sites.
The more cross-signaling that ends up existing, the more likely you won't just suffer from the accumulated 301 hop-hop-hop issue, but it will be compounded by those other signals.
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My first recommendation would be to make a decision and stick to it! If you do want your pages to rank then it's best to stop changing the URLs!
As you've no doubt found, changing your URL approach can give you real headaches managing 301 redirects.
While it's nice if you can get your keywords into the URL, it's not a total disaster if you can't. This is just one of many many factors that are going to affect your ranking and performance of your page.
You've got to consider the return on investment on your time. You are almost certainly better off spending the time creating better on-page content for your customers - rich, compelling and informative product pages, clear benefits, testimonials, calls to action etc than spending your time trying to manage your URLs.
Can you adopt a hybrid approach and give you key products /money pages manual optimised keywords and leave the lesser pages as dynamic?
Are your individual product pages actually the ones you want to rank for your keywords? What about your category pages?
What content on your site is currently earning you authentic links?
Can you provide useful resources for your customers to help them chose the right products? What are the specific problems/concerns your customers have - what can you do to make their lives and their decisions to buy as easy as possible.
Can you get some testimonials - (not just generic comments about your service but also how specific products benefited your customers, overcome problems they had?
For example (Durability) "My old stuff wore out after a matter of weeks, these fantastic things from x have still look great after a year!"
If the URLS are reasonably sensible - don't sweat it - use your time to improve other aspects of your site.
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This is what are the differences between dynamic and static URLs (by Google):
http://googlewebmastercentral.blogspot.com/2008/09/dynamic-urls-vs-static-urls.htmlIn short it's that static URL have a slight advantage in terms of clickthrough rates because users can easily read the urls, but the decision to use database-driven websites does not imply a significant disadvantage in terms of indexing and ranking.
Anyway the URL is static or dynamic you should keep them in one place, because redirecting a URL to another loses up to 10% value. You can read more here: http://www.seomoz.org/learn-seo/redirection
Hope this helps.