Well, I could probably answer all of your questions, but that would take all of the fun out of it for you. But, I will get you going in the right direction.
Here are some tools that will help you with the answers that you are looking for. The pages that you want to optomize would be one page for each 1 or 2 keyword phrases that you are trying to rank for. Are the links in the center columns going to go to pages from the home page, Im assuming that they are, but just making sure, otherwise I like the look of it. Very clean and easy to get where you are going. Most of the dynamic pages are indexed by google. You can check this by useing the search in google site:pitmanskills.com, you will see that a lot of them are indexed. They might not get good page rank because they are a couple of clicks away from the homepage, so there is page rank drain before you ever get to those pages.
Here is a tool to research keywords. Start with something that you know that you want to target, and go from there.
http://www.digitalpoint.com/tools/suggestion/
And another one at
http://www.webmaster-toolkit.com/key...rch-tool.shtml
Here is a tool, free trial that will measure how competitive the search terms that you think you are going to target.
http://www.wordtracker.com/
site is currently down, but Im sure it will up some time today.
Hope this helps.