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One of the main things I have my eye on is making it much easier for users to upload files to the server. Making a post or a comment is easy, but getting even a small binary file, like an image, is a few more steps, and getting a large one (say, over a meg) is ridiculous - you need to leave the browser entirely and go through a bunch of convoluted steps.
I am looking at the uploading issue from a lot of directions. I think that email is going to be an important upload channel, especially from mobile devices. And I'd like to see some integration with my desktop tools which for me would mean iTunes and iPhoto. I want to have a playlist in iTunes and an Album in iPhoto, and any song or image I put in them is automatically put onto the server. I actually have this working in iPhoto, except you have to click on a program in the dock when you want it to upload - but then it will put everything in that album onto the server and erase the images from the album.
But we really need to be able to upload larger files through the web upload interface. This works fine for things under a meg, but above that it craps out. This is because of the way Apache handles these file uploads. Lighttpd is another, newer, open source web browser that aims to fix this problem. And a few others that will be important to us as well. Seems like this is the web server to use (at least it will be when they get all the kinks worked out) if your site deals with a lot of large binary file uploads and downloads. Here's the Lighttpd homepage. And here's the explanation about large file uploads.
I'm going to still mainly run Apache, but I hope to have Lighttpd running as well for certain virtual domains that deal with its' sort of thing.