I've been listening sporadically to Buddhist Geeks for a while, and as I go back and start to fill in the gaps it's interesting how many really good episodes I missed along the way.
For example, I missed the posts that talked about Dharma Overground, a site I mentioned before that has been very helpful.
And the posts about Kenneth Folk, who related the stories of the Burmese/Mayasian Theravada culture, where enlightenment is seen as very real and very possible, as opposed to American Zen practice, where such attainments are never talked about and their likelihood is characterized as pretty much nil.
And here is one map of the territory, the Progress of Insight by Mahasi Sayadaw.
Stephen Snyder and Tina Rasmussen have a site called Jhanas Advice, which has links to a number of their talks. They also have a book, Practicing the Jhanas, based on their experience and with the endorsement of Pa Auk Sayadaw.
Stephen and Tina also have some stuff at Dharma Seed, which has a lot of Vipassana talks.