I discovered Lullabot recently and I'm getting caught up on their poscasts and screencasts. It's great insight into the Drupal community and Drupal development.

Here are a couple of good ones to get started with images and media:

Drupal Voices 43: Aaron Winborn on the Media module

Exciting development in the Drupal Media model. This sounds amazing.
http://www.lullabot.com/drupal-voices/drupal-voices-43-aaron-winborn-med...

Photo galleries with Views Attach

Great screencast by Jeff Eaton on how to build a photo gallery. I've had some issues using his exported Features configuration, so I've just used this as a guide and found my own way.
http://www.lullabot.com/articles/photo-galleries-views-attach