Before I went on vacation I implemented a new image gallery based on this PhotoHandler project on Codeplex that was pointed out to me by Todd Lewis. We already had a photo gallery feature but its a fairly low frills thing, you have to upload images one at a time. My thinking has been that eventually I'll implement one that integrates with Flickr and some day I may yet do that.
The new one was pretty easy to intgrate into mojoPortal, it allows you to just point it at a folder containing images and it does the rest, creating thumbnails, web size images etc. So the idea with the new one is you organize the photos into folders on your local machine then upload the whole parent folder using an ftp client like FileZilla or whatever you use. The folder(s) need to be uploaded to Data/Sites/[SiteID]/foldergalleries folder, but from there you can nest them any way you want.
I did implement a feature for uploading files but the ftp approach is the sweet spot.
You can see my vacation photos using the new gallery here: http://www.joeaudette.com/photography.aspx
Notice how it makes a thumbnail for the sub folders by amalgamating the images contained in it into a thumbnail
So there are 3 top level folders, ChichenItza, resort, and skyline
Its available now in svn trunk for developers and will be in the next release which will probably be in the next few weeks.