I have always thought that drupal has serious shortcomings when it comes to handling image. As usual with Drupal, there are a significant number of ways to get image handling capability. The following modules provide it (in no particular order) :
- acidfree
- gallery
- image
Those 3 modules are interesting as they tackle the same problem in 3 different ways.

• acidfree is a full featured image/video/gallery tool. It provides a new content type (acidfree media) and basically does everything for your when it comes to creating, deleting, modifying and displaying media files. Its main problem is in its interaction with other modules such as views.It also depends on the filemanager module which I don't think should be necessary.
• gallery embeds the famous gallery2 into a Drupal installation. As I wanted a pure drupal setup, a third party integration module was to be discarded. This could also make theming tricky.
• Image seems to be closer to the "drupal way" than the above solutions. It just provides a new node type called image. It comes with two other modules image_gallery and image_attach which add features to the new node type. it also comes with an image processing toolkit based on ImageMagick instead of the built-in GD2 toolkit. Its main drawback is its initial complexity for beginners and I think it was why I chose acidfree to manage the images of this site.

It's when I have wanted to a view of acidfree nodes that acidfree clearly showed its limits. Acidfree needs to put more abstraction into its content type to interact with views properly and it also needs a better theming support as all the theme_ functions available are a bit confusing and overlapping. Default theme should also get rid of table in favour of div in order to better separate presentation to content (among other advantages)
The good news is that acidfree seems to be getting there with its future 5.0 release :

Acidfree-cvs.tar.gz is doing its best to keep up with HEAD. I am currently doing a complete rewrite of Acidfree so that it fits in better with the Drupal way. It will use the Taxonomy, Image, Video, and Views modules to create an interface that is very similar to the current version of Acidfree. However, since it will be based on other node types, it fits in with the Drupal Way better and should give a better unified media management system to Drupal. If, by chance, I don't make the deadline, or people don't want to switch modules without warning, I will provide an 'Acidfree_legacy' module which will simply be the current 4.7 Acidfree ported to 5.0. The upgrade path will be part of the standard update.php script that will be shipped with the 5.0 version of Acidfree. Really, you shouldn't have to do anything special to upgrade when the time comes.

I don't believe upgrade will be as easy as that. Acidfree nodes will have to be migrated to image node and the same thing for video nodes. i might be pessimistic but I expect migration to be somehow tricky if not painful as it could include a manual import or recreating of the image nodes.
The good thing is that once released acidfree5.0 will essentially be a gallery with extensive theming features and media management and organization will be left to other modules.
I will certainly be playing around with the image modules on this site in the very near future in order to migrate across so you might notice a few issues on the galleries. sorry for that.