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I use the Google XML Sitemaps plugin to automatically generate my sitemap for my blog. You can have more than 1 sitemap for a site so you could create a 2nd sitemap for the static pages & manually manage this as static pages are less likely to change. If the static pages are part of your Wordpress install then the plugin will pick these up too.
I would build 2 sitemaps for these files, 1 XML sitemap and 1 HTML sitemap, separate from the main sitemap and add these to Google WMT. The HTML Sitemap could also be used as a directory for visitors too.
Where possible link to the documents from the site too, this will increase the chances that the assets are indexed by Google.
Hi Dave
From what I can see the site is in the Google index after I searched info:www.specialtysealgroup.com
A quick search in OSE shows me that you only have 2 links pointing this page a PA of 19 and DA of 8
Your clients competitors will no doubt have much higher PA/DA and lots more links to their pages, and therefore Google will value these pages more than your clients.
I recommend you consult a reputable SEO agency to discuss a link building campaign.
When did you change your meta description was it in the last few days?
Have you tried to add this:
<metaname="robots" content="noodp,noydir">Without looking at the site, I couldn't tell you what's causing the problem but Google could be pulling info from the open directory, this tag will force Google and Yahoo to use the description you give them</metaname="robots">
Google do not always show the meta description. If they feel a more meaningful snippet can be had from the content, it will take something from there. If you have little or no content (say just images) then Google does not have much to show.
I recently wrote a guide to link building and traffic generation using Scoop.it
http://www.rootswebsolutions.com/social-media/content-curation-web-traffic-scoopit/
It's just been promoted to the Scoop.it's own account.
There are people on Scoop.it who already receive hundreds of page views per day to their pages.
So by suggesting your own content to their page you have a chance that your post will be accepted and a good percentage of their fellow Scoopers will come flooding to your site and re-scoop your page to their followers and other social networks too.
Dave,
Assuming your 301 redirects are technically correct then it will take time for your new page URLs to be indexed by the major search engines.
Be aware that your rankings may not come back 100% as they were before the change.
A 301 redirect does not pass all the PR and linkjuice as many SEO's assume. You can read about it in this interview with Matt Cutts and in this illustrated summary from Rand on SEOMoz
From my personal experience what you are seeing is normal just keep doing the good work you are currently doing a quite Google search with info:yournewdomain will show if your new domain has been added to the index.
If you are starting out then I recommend the Hostgator baby croc package they have absolutely brilliant support and all the scripts and features you will ever need from cPanel hosting.
Hope that helps 
For keyword research I like to use the Google Adwords Keyword Tool.
I have also used Market Samurai in previous roles which is a great tool for analysing the whole market for that keyword e.g. competition, back link sources however it is a paid service.
This blog post over at SEObook has some reviews of free to use or trial keyword software