Multiple File Upload Field with Drupal 7
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Transitioning over to using Drupal 7 has been very frustrating these past few months - after the lengthy process of encouraging the Drupal Community to help updating core to reflect some user interface improvements over Drupal 6, that energy for making processes simpler hasn't seemed to carry through to contributed modules.
Particularly, all the CCK advancement for media handling through fields that had happened with Drupal 5 and then 6 seems to have been thrown out the window with the horridly infantile state of the Media Module, which is reason enough to hold off on upgrading and stick with Drupal 6 for a few more months... yes, while the core team races to plan for Drupal 9's life-changing improvements, I would still recommend making things work well using Drupal 6, a proven platform.
Still, you may be inclined to use Drupal 7 and then start pulling your hair out when you realize that the Media Gallery module doesn't really work well (lock in to 1 type of lightbox etc...) and yearn for old CCK methods for using imagefields which can handle multiple files being uploaded at once via flash or AJAX using contrib modules, of which there are many options these days...
Fear not - there is an experimental approach that works and is currently being developed further using Plupload which is being lead by vingborg called Mupload - I recommend checking it out and using that cash stored in the toupe fund for something else.