@Justin - I had a look at your site and it looks like you're loading your podcast episodes by adding them to a 'podcast' category in your blog posts. SSP does not work this way - you need to add your episodes under the 'Podcast' menu in the WP dashboard otherwise they won't show up in the feed. Apologies if I'm wrong, but that's how it appears things are working on your site.
@KwonFiveNine - It looks like you're doing things correctly, and your podcast feed (http://speakliferadio.com/?feed=podcast) looks perfect and reports no issues. When you submit that URL to iTunes, what error are you getting exactly?