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Google penalizes duplicate content which is deceptive, spammy, thin content, etc. If it's necessary duplicate content (like T&C legalese) then at worst they probably won't pass any equity to it. Here's an article on a Matt Cutt's video about Duplicate Content from July of last year http://searchenginewatch.com/article/2284635/Does-Duplicate-Content-From-Terms-Conditions-Affect-Google-Rankings

This just reminds me how much I hate the Top of Page 2. Its one thing to be further down in rankings and know I need to put in the extra effort, its another things to be trapped at the top of page 2 and wracking your brain to figure out why sometimes a page just won't break that ceiling.

I've had this issue twice in the past. Once was because of a conflict between All In One SEO and another plugin which was fixed by updating the plugins. The second time was after a theme change where it turned out the theme had an internal suite of SEO tools that were adding the secondary description which was fixed by shutting off those features. Without knowing all the details of your wordpress site, its a bit hard to determine the exact cause. Check that your theme doesn't have a function interfering with All In One and try turning off plugins to see if any of them are in conflict. Could be as simple as needing an update.

Well, to start... I tried crawling your site with Screaming Frog and of the 41 pages it found: 21 were 403 Forbidden. I was able to view those pages fine in Firefox though. Open Site Explorer is showing no external backlinks... so you need to work on getting people to link to you as well.

The canonical should pass link equity similar to a 301 redirect.

I agree with Everett from a standpoint of User Experience. It could potentially be better for users if they appeared on a product page where they could then choose color, size, etc. variables for their product instead of having to click through multiple pages to find the right one or scroll through a huge list of variations.

The reduction in pages should also help consolidate link equity and keep pages from cannibalizing each other in the SERPs.

As for Takeshi's suggestion on Canonicals, I'm a fan of the rel=canonical tag but the potential problem with using them in this instance is twofold. 1) As Takeshi mentioned: "as far as Google is concerned you only have 1 page with the content on it" and 2) Canonicals are suggestions not directives so the search engines may choose not to recognize it if not used properly.

How similar/different are these products? Are they marketed to slightly different audiences? Do they have slightly different uses? Or are the essentially the same product but one is blue and the other is black? If they can be marketed to different groups or have a big enough difference that they should be separate pages then I'd consider doing some research and copywriting to add unique, relevant content to each to set them apart. If they're really too similar then determine whether they definitely need to be on separate pages still or if the could be merged. If they can be merged, choose which on stays live, update the page as needed and 301 the old page to the one still live. If they definitely need to stay on separate pages still despite being so similar, consider canonicalizing one to the other.

Similar to what BJS1976 and Takeshi stated, the way we handled the bulk of duplicate content issues from a similar circumstance for our ecommerce site was handling the different varieties of the same product through parameters and then canonicalizing the parameters to the version of the URL sans parameter.

For example, due to database reasons /product1.php?color=42 and /product1.php?color=30 are the same product but one is red and one is blue, the pages are exactly the same & have radials/buttons/dropdowns to choose any available color, /product1.php would default to one specific variation we chose (usually the best selling color) and then /product1.php?color=42 and /product1.php?color=30 had a rel=canonical tag added pointing at /product1.php

For any remaining products flagged as duplicates that couldn't be fixed that way, we set those aside to have myself and another copywriter work on creating further content that would set them apart enough as to not be duplicates.

And here's a Matt Cutt's video on ccTLDs from July of last year http://youtu.be/yJqZIH_0Ars

He also references how they handle those "cool" ones like .ly, .io, .it and so on.

This is a common problem in WordPress. The tag archives, category pages and author archives can create many multiples of the same content and cause numerous duplicate content issues. Most people choose to NoIndex their archives since they have potentially little Search value but they do/can have value from a User perspective. Setting posts to show snippets on Archive pages can lessen some duplication issues as well. You should also double-check the tags you are using as one-off tags can cause a lot of problems with duplication. If a post has 7 tags on it and those 7 tags are only being used for that one post, you now have about 10 versions of that post sitting on your site. Make sure to only use relevant tags and that the tags used are then also used as needed on future posts in order to tie together related posts. All the functionality to NoIndex archives and change posts to snippets can be found either as part of your current theme or the Yoast plugin is a good download to help manage those things.

Typically a ccTLD is suited for that specific country/region. So having a .co.uk will make you more relevant to searchers in the UK but not for searches from say the US looking for something in the United Kingdom (unless they happen to be searching through Google.co.uk). This is not 100% always the case though but generally so. If you're attempting to globally reach people searching for that term, you'd probably be better off with a generic TLD.

Looking at the two options you gave, I'd say it depends on how you handle your site navigation (If you're able to make the URLs however you want and aren't restricted by your CMS). For example, if from your homepage you have a category page/hub page for Services and then from there you can go to Service1, Service2, Service3, etc. then I would think company.com/services/service1.html is the most logical way of structuring your URLs. If there is no Services category page (or your homepage is essentially the Services page) then company/service1.html isn't a bad way to go. Personally I'm a fan of creating category/hub pages and more site content where relevant so I'd go the first way, create some great content for a hub page and then make sure the services funnel down nicely from there for the more targeted/longtail searches.

I completely understand wanting to target both. Since your title tag is too long, it seems to me that it would be better to choose one of the other to shorten it. Keep it in page copy and meta description where natural though... don't go changing that. But your title needs to be closer to 64 characters long. Plus Google takes into account pixel width to determine how long a title can be before it gets truncated.

As to the redirect. Link equity does get passed with a 301. As long as the links are relevant, authoritative, and/or not spammy then that's a plus.

Your title tag is too long and repeating "portable dvd player" twice in the title looks unnatural personally. Yes, I know one is "player" and the other is "players" but Google already understands plurals so its not always necessary to hit both the singular and plural of something in copy.

Checking Google Page Speed Insights, you're scoring a 57/100 on the site. I'd look into some of their suggestions to improve user experience.

I'm not finding any external links to that page using Open Site Explorer. You might want to bolster the page with some good inlinks and social shares to give it a boost.

What HTTP status response codes are they returning? If they're a 200 but providing a poor user experience then eventually they'll be deindexed or at least ranking so poorly that no one will run across them, if they 404 or 410 then they'll be deindexed eventually, and if they 500 then you likely need to fix some other things on your site. Also, are you losing any link equity by not 301ing them?

Are they listed in Google Webmaster tools? You should be able to find out where they are linking from that way. Also, if they're 404ing and they weren't ever a real page and they aren't really being linked from anywhere then there's no real reason to stop it from 404ing. You should probably make a custom 404 to serve people that directs them back to your site instead of a completely blank page.

The keyword tracking tool is for organic rankings.

Nope, that wouldn't cause a blanket penalty on the term. Just didn't have the time that ImWaqas had to go over things in-depth but wanted to at least point that out since I had the chance. Take a look at all the things ImWaqas stated to help fix your major site issues.

One oddity I did notice, you have <meta property="<a class="attribute-value">og:locale</a>" content="<a class="attribute-value">en_US</a>" /> listed in the page source which i believe should be en_GB for a UK specific website.

I agree with Federico and Keri. Don't shoot yourself in the foot by removing the old info just to make it a 2014 post when you can keep the old post (which is still very relevant for its year) and have a new post that will be relevant for its year as well. Plus the idea from Keri is a good way to organize them together, increase user time on site, and could help to lower bounce rates.