A few of the top items that Google Webmaster Tools tracks that you should be aware of:
1. Duplicate Title Tags
2. Percentage of keywords (a literal count of how many times a keyword appears).
3. Top pages linked to from within the site. (ie which page is getting the most links from within your site).
4. Top pages linked to from out on the web.

With these few data points, a search engine could determine what pages are most important to the site owner, what pages are most important to the web community, and what pages have the most relevant content for a keyword match.

One strategy might be to make sure that all of these categories are congruent for each keyword. For example, the page that everybody else links to the most = the page you link to the most = the page that has the highest number of keyword appearances.

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