Dougal Campbell's geek ramblings

I’m looking for advice on two seperate but related projects.

First of all, I want a good way to manage images for right here on my blog. Obviously, I want something that integrates into WordPress. Ideally, it should allow me to organize pictures in some sort of hierarchical directory structure, annotate pictures with metadata (title, date, place, categories/tags, etc), browse pictures in various ways, generate multiple sizes, and so forth.

The second one will be a standalone site for family members to share photos with each other, so it doesn’t necessarily have to integrate with WordPress. However, it should be multi-user, and super user-friendly for the non-techs. I was looking at Coppermine Photo Gallery, but I’m not very happy with the interface. I could also just point everybody at Flickr, but I think it would be too overwhelming for some of our family members.

Any recommendations?