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Google will do just what you described - drop the old pages shortly after starting a 301. The new target of the 301 could take 1 - 3 weeks to make it back into the index - but it will.
Good news is that if 1-3 weeks is too long for you, you can remove the 301 and be back in with the old page in a few days.
back in a few days assuming googlebot visits your page regularly
My url was: [my-web-host.com...]
Over time I set up all of my sites in directories like:
[my-web-host.com...]
If the site performed well then I would license a domain like:
[new-site.com...]
The new site would basically just be pointed at the same files. I now have three domains that have "grown up" this way. I realized that Google was indexing all of the files both under the virtual path and the domain path. This was causing duplicate content penalties for my domains. The more files I added to the site the worse the PR and ranking seemed to get. Follow this with weeks of brainstorming with my webhost.
What we first decided to do was to disallow the virtual paths at the webhost root level. Then we decided to add permanent redirection to the .htaccess files so that Google would:
1 - Delete the [my-web-host.com...] listings from their index
2 - Follow the permanent redirection directive to the files in [new-site.com...] and change all references to the virtual name files to the domain name.
Logically,this seems to be the airtight solution. It solves the duplicate content problem and also causes one set of listings to be "combined" into one set of listings just referencing the domains.
Will this work as outlined?
The key to all of this is to change your internal links - and ask others to change their links - so that the search engines become aware of the new URL before you install the redirect. Once the SEs which are important to you have picked up the new URL, you can install the redirect without much worry.
You shouldn't have to do this, but right now, it seems to be necessary. We've had enough reports like this one that I believe it establishes a trend. I also believe that it is something that needs to be fixed, and that it will be fixed. G should hold off dropping URLs which respond w/301 until after the target URL is indexed.
As to "duplicate content penalties" in the interim, either choose to risk it, or don't change URLs. Duplicate content "penalties" in this case are simply the result of dividing existing PR between two URLs, though.
Jim