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The domain I am moving it to has very little links to it and is not as old.
I already know because I've tested it, that when I 301 redirect a page from the old domain to the new domain, it ranks pretty much the same way it always did once it gets re-indexed by Google for the new domain. One question I have is, If I create new pages on this new domain, are they going to rank the same as new pages I would create on the old domain (which always ranked great out of the gate)?
I assume passing PR to the new pages will help, but am I looking at a situation where all the old pages from my old domain that are 301 redirected to the new domain rank well, but any new pages on the new domain will not rank well?
Most of the time, my experience is that once the newer domain is ranking well on the old urls (and that can take anywhere from weeks to months) then you can create new urls that will also rank well -- although it does seem to take just a bit longer. That might just be my impatience because I haven't kept any hard data, but that's the way it seems to me.
Your situation, as I understand it, is that the target domain for your 301 has some backlinks and is already ranking before you move the urls from the other domain. That's a hopeful sign to me that you will be able get new urls to rank quickly.
Most of all, if you make this move, then do it with full commitment and technical precision. Otherwise, if you do it tentatively and then there's a rough patch and you back out, you will be sending some strong signals that you are trying to manipulate Google, and they will not like that.
I was also wondering, if I already 301 redirected some pages (like 1000) to another directory on the same old domain, but now I want those pages to 301 to the new domain, do I put the 301 on the original page or on the page it was 301'd to in the same domain but different directory?
I'd study each of your urls carefully to see which ones have external backlinks and which ones currently get search traffic. If there is no search traffic and no external backlinks, then a 404 is fine. Don't start throwing around 301 redirects like chiclets.
There are some threads that go into more detail in our Hot Topics area [webmasterworld.com], which is always pinned to the top of this forum's index page. Make sure you handle canonical situations properly on all your domains, and avoid creating redirect chains while doing that as well. Every url where you employ a 301 should go through just one redirect and then land on the proper url.
So if this /domain1/page1.htm now 301'd to /domain1/page2.htm
and now I want /domain1/page2.htm to go to /domain2/page2.htm,
So, do I want to re-do the first 301 (/domain1/page1.htm) and the new page (/domain1/page2.htm) 301 to BOTH point using 301 to the new domain /domain2/page2.htm?
This way, there are now chains, right?