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At least go into the "Crawl" section in Webmaster Tools, and do a "Fetch as Google" of your domain and all pages. This will ask Google to reindex your whole site. You can also see your page the way Google sees it.

He needs to start with the obvious first. Take a look at Webmaster Tools to make sure Google is indexing his pages. Do a Fetch on some pages to see what Google sees. Next move would be to have a full, in depth site audit done to review all the elements of the site. Screaming Frog is a good tool for that. Then he needs to go back and explore his links again. Adding some new, relevant links will help.

I recall Matt Cutts, in one of his videos (https://www.youtube.com/watch?v=z07IfCtYbLw), addressing product descriptions (Scraped from the manufacturer) with E-Commerce sites, especially those sites that are selling products that a hundred, or even a thousand other retailers are selling. He said that you would be ahead of your competition if you took the time to rewrite those descriptions, so they are original and not duplicate content . It is not necessary to refresh or rewrite them every couple of months. Just having a unique description that no one else has for that product will put you ahead of everyone else selling that product.

It would be a good idea to try and get your customers to write reviews on your products and post them on your product pages. This is unique, original content that is fresh. Amazon is a good example of doing this.

The fact that you have all new URL's, even though you have 301'd all your old URL's, it will take Google time to crawl, index and rank those new URL's. It is like a whole new website, and is not currently in Google's database.

You might try going into Google Webmaster Tools, under the Crawl section, and then Fetch as Google. When it is Fetched, click on the Submit to index button, and then click the box "URL and all linked pages". It may speed up the process of Google re-indexing, but is no guarantee.

I have had to do this on numerous sites where I wanted to change to different URL structures.

Sure. First off, you've been asked by the linking company to do so, so you want to accommodate their request, and secondly, it will do you no harm.

Google is getting pretty good at sniffing out webmasters trying to game the system. Just naturally put your keywords in places that make sense and try not to overdo it, and you should be fine.

It is going to be spamming your URL's with keywords that are not serving a subfolder purpose. I would focus on naturally putting your keywords into your product name in the title tag, URL and H1 tag.

Might be a little spammy in your title tag with "Las Vegas"

With my company, which has several major domain sites and a mother-ship root domain, we've had this ongoing discuss of moving all our subdomains to subfolders. Our concern is the pain of the transition in losing valuable traffic until the subfolders gain value and traffic. So we have the following subdomains:

boatcovers.iboats.com

boatpropellers.iboats.com

biminitops.iboats.com

forums.iboats.com

And all our other products are listed under iboats.com. Is there a painless way of making the switch to move our subdomains into subfolders and not get killed on traffic?

We are considering adding expires header to our site. If we add this meta tag to expire for a certain date, but we do not make any changes to the site after it expires, can you be penalized for this?

Rob:

If you haven't done this yet, research the keywords for your business. Make sure you use these keywords in a natural way on the pages of your website. For each page, put your main keyword in the title tag, url and H1 tag. Depending on the website platform you are using, you should be able to do this fairly easy. Make sure that you have keyword specific alt tags on all your images. Get your website listed with all the online local listing directories, especially Google places. Set up Facebook, Twitter, Google plus and Tumblr pages. Work with industry related websites to mention (citations) your business and website.

Keep in mind that all your content on your web pages and social channels need to be engaging and natural. With the launch of hummingbird, it appears that Google is looking more for themed and topic-based web pages, so give the users what you think they are looking for.

There are a couple of things you can do that will help your product pages rank better over your pdf pages. You can do a canonical from the pdf to the product page it is referencing, giving your product page the ranking value. You can incorporate your pdf into text (html) on your product page, giving your product page additional, relevant content, thus boasting ranking.

Dave:

Thanks again. I just watched Rand's whiteboard Friday on this, and it gave me some additional ideas on some old sites that we have, to utilize the value of those pages by canonicalizing those pages to our main website.

I usually watch a lot of Rand's whiteboards, but must have missed this one.

Thanks!

Craig:

Thanks for your input. We are trying to determine how best to maintain the traffic and value on our outside engine site, but still give our boaters on the main page the info they are looking for without clicking away to another (manufacturer) page. Having duplicate pages makes sense to us, but making sure that Google gives the manufacturer page the value. So a canonical seems logical for what we are trying to accomplish. We have hundred's of thousands of pages on our main site, so we are not concerned of losing value there. However, we do want to keep and build the value of our manufacturer pages. That is where we want our traffic to go when they are looking for that manufacturer-specific product.

Thanks again for your input!

Thank you for your reply. I'll check Rand's video. I'm assuming it is one of his white board Friday discussions? In the meantime I did find Google's take on it. It was on their Webmaster Central Blog: http://googlewebmastercentral.blogspot.com/2009/12/handling-legitimate-cross-domain.html

Thanks again for responding!

We are a boating site and have our main site with all it's products. We have an engine section within our main site. But we also have an outside domain, specific to a certain manufacturer of engines. So we want our customers to still find the engine information for this manufacturer within our main site, as well as find the manufacturer targeted engine site in the SERPS.

My question is this: Can I canonical those pages within our main site to pages on the outside domain? Or does are canonicals to be used only within the same domain?

Thanks,

That's why you are not sweating the Penguin update... you think and breath like your father.

I'm not particularly concerned. I'm banking that as Penguin 2.0 takes down my competitors spammy links, I will climb in rank. I do have competitors that have some really bad neighborhood links. So I'm counting on the update to reward us.

As for your Mom... are you the result of your Mom's one night stand?  

I'm waiting, probing and analyzing and haven't seen any signs of a Penguin change. I am seeing some of my head terms bounce around the last couple of days. Mostly bouncing up and then back down again. I'm not sure if these are signs of an algo change starting, and working through Google's servers.

Has anyone seen anything yet?

Thanks Takeshi.

I am using Open Site Explorer, and notice a drop there too, but realized different results with the addition or exclusion of "www".

I have used the other tools you mentioned. I just wanted to make sure that Google wasn't trying to mask or restrict our access to seeing website's backlinks. That could really hurt our abilities to build backlinks.

Thanks for your input.