One of the biggest challenges Drupal presents is dealing with media files. Because of the open nature of the product, there is usually a lot of time needed to make something as simple as an image gallery. I spent many hours designing one myself using different image handlers, a custom content type, views and HTML entities that present
Packtpub.com has a great resource for those who are dealing with media files. I just picked it up but it looks like it is going to be a great resource for me. I specifically plan to use it for a video based help system for the website that I am currently working on. But check out the book at the link below.