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Hi mcardenal. Given you're a newbie you might just need to walk yourself thru the site and make sure all your title and description tags are unique. Your site is not huge. I would start with a screaming frog crawl of your site. The basic software is free. It's an extremely easy way to crawl your site and quickly and easily find duplicate tags. If you're looking for a more indepth answer to your question, keep reading. A standard Wordpress installation isn't SEO friendly. But you're in luck! Back in February there was an advanced SEO webinar hosted by SEOMoz and lead by Nick Herinckx. Nick explains what you need to do maximize your findability. Here's the link to the webinar - http://www.seomoz.org/webinars/advanced-wordpress-seo. It runs about an hour and a half including Q&A, but it's well worth your time to watch it. You have unnecessary repetition in your tagline as well. "Conquer student student debt!" You might want to fix that at the same time.

Hi mcardenal, you should not use OSE for checking if your site has crawling issue, but the crawl report. And remember, the Moz crawl report can be ok if your site own a limited number of pages. If it is composed by undreds of thousands pages, then the Moz crawl must be considered more a parsing than a complete crawl. For that reason, even if the Moz crawler is an amazing tool, which present very well the biggest issues a site may have (especially exact and substantial duplicated content issues), for having a complete crawl of your site as if it was crawled by Googlebot, I suggest you to use the Screaming From Spider SEO. With that tool you will be able to understand if bots can access correctly to all the pages of your site. OSE is a tool for analyzing the link profile of a site, not its state of indexation.