SEO/Changing File Structure/301 Redirects On Changed URLs - Now What?

Question

I have a fairly large website that has been around forever with hundreds of #1 and first page ranking pages. For many reasons, I have decided to pretty much completely overhaul my site structure and switch from a predominantly flat file structure to a predominantly structured file structure (say that 10 times real fast!). This overhaul is such an enormous undertaking.

Anyway, needless to say, the urls have to change. Two important things to note are: 1) My money pages are geo targeted. And, 2) All of those pages have been targeting around 6 keyword phrases each (per city/state). Due to a huge increase in online competition, a lot of those pages that have been #1 forever might only be #5 - #7 now. I need to be #1 again! So, I feel that the pages will become much more ULTRA relevant and tidy only targeting 1 - 2 keyword phrases per page. So, in other words, my website is about to triple + in size... sigh Anyway, I have done about 100 pages so far as a test and everything is going perfectly according to plan...

Here is what I have done (for each page):

1) Changed www.mysite.com/long-page-url.php to www.mysite.com/sub-directory/subdirectory2/short-pageurl.php

2) I 301 redirected the old urls to the new urls in my .htaccess.

3) I changed all of the old urls in my site navigation (and added a ton of new ones) then generated a new sitemap.xml and re-submitted it.

4) I fetched and submitted each new url in Webmaster Tools.

Within a few short minutes all of the new pages were already indexed and coming up between #1 and #5 in the search results for every key phrase.

Here is the confusing part... Remember, each of the old pages, which were targeting about 6 keyword phrases have now become 3 pages, which are only targeting about 2 keyword phrases each. Sooo... I am seeing where the old re-directed url listings AND some new url listings are showing up one above the next for certain searches. This is because the old page was optimized for multiple keyword phrases and the new pages are each optimized for 2 of them, etc...

So, finally, here are my questions and concerns:

1) It's my understanding that Google will eventually pickup on the 301 redirects and the old url listings will drop off of the search results and be replaced with the new urls. Is that correct? Any idea how long that usually takes on average?

2) Do I need to be concerned about any duplicate content issues? My site is all pure HTML5/CSS3, by the way. Not CMS. No crappy Wordpress ever again for me! But, that's another story...

3) Is it alright to delete all of the old pages that are being redirected? If so, when? After they have dropped off of the search results and been replaced with the new corresponding pages, perhaps or do they even matter anymore?

4) Can the 301 redirects ever be removed from my .htaccess? Personally, I don't think they can ever be removed, due to past experiences I had when I converted my whole site from .htm to .php and then again when I went from http: to https:. I just want to be sure, because this is a little different...

Answer 1

Any idea how long that usually takes on average?

Google timing is always an educated guess at best. Don't be believe any different,

Do I need to be concerned about any duplicate content issues?

No need to worry about duplicate content, between the 301 redirect and submission to Google Webmaster Tools, everything will work itself out.

Is it alright to delete all of the old pages that are being redirected?

I would not delete anything until you see indeed all your new pages are working and there are no signs of old listings, just to be safe, unless security or bandwidth plays a role.

Can the 301 redirects ever be removed from my .htaccess?

It doesn't hurt to keep the 301 redirect, were are talking about a few short lines of code and if people have your old URLS bookmarked I would rather have a 301 redirect in place than returning a 404 error, which could hurt. Unless you are talking hundreds of redirects. How many do you have?