@Jake Goldman - I've always seen TimThumb as a terrible solution to a very real problem. The thinking behind it was good (provide an easy way to resize images on-the-fly) but the execution was terrible (let's expose that resizing functionality on the front-end and potentially open up a huge security hole).

Sad part is, most of the functionality that TimThumb provides, I was able to replicate in a recent plugin entirely using internal WP functions.