Why do you care, where the server stores the images?
It is important that the end result is categorized, right? You want the user to see “family fotos” and “event fotos” and “funny fotos” etc.
So just ignore where WordPress stores the files you upload and concentrate on the display of the images.
You might want to look into plugins that display images associated to posts. Search for “post image”. Or download my plugin called EasyPermGals. What this does is show a gallery of images that are uploaded to the post. All you need to do is create a post, then upload the images. No need to manually insert it into the post, no need to actually care, where the images are stored.
It’s important to realize this fact: upload an image into a Post, and it is associated with that post. So, if you call your post “holiday fotos”, you basically have a “category” that you can show your fotos in.
Otherwise you might want to check out “big” gallery plugins.
But I think that is unnecessary, I like to keep things running on the “basics” of a site, and that is, in the case of WP, posts and image uploads.