Rebranding & a Url Structure Change
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Definitively, changing your domain it's a bad idea. You can recover part of the seo but probably you can lost some.
For the url changes, i can recommend you to make a catch-all file who evaluates the requested URL and make a 301 redirect to the new URL. That's the better form to try to mantain the seo of each page.
But, for my experience, you'll be losing something at this change.
The best idea it's not change the domain, and if you can doesn't change the urls too. If it's neccesary, do it but make this page first and test it, for having a clue for search engines and users. Later, you can try to contact the pages who have a link to your page, for changing this link.
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Thanks but I was wondering specifically if you change the URL structure with the redesign of the homepage and site will it be a bigger loss of SEO than doing the redesign and then doing the URL structure change months later.
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This is a really tough one to answer because while there are examples of companies doing this in stages and examples of this being done all at once, it's impossible to know what the results would have been if any one example had been done differently. I am tempted to say that the more changes you can make all at once, the better.
The reason for this is that if you go through one set of big redirects to go from www.domain.com/url-structure to www.newsite.com/new-url-structure, that's only one set of redirects Google has to process. If you do this in too many stages, Google has to find and process each set of 301s every few months.
The more times you 301 a URL, the less authority it seems to retain from the original URL. This is disputed and debated, but it definitely still seems like a poor idea to go through more 301s than you really need to. 301s can definitely result in temporary ranking problems, so the fewer of these you need to endure, the better.
That said, this is a huge task with a lot of changes and it doesn't sound like they'll be able to do the whole thing at once?