OK, not funny anymore. 
Robert Scoble couldn’t get WordPress.com upload feature to work…
Dave Winer wrote: “Lots of food for thought in my meeting on Saturday with Nick Denton. They're big users of blogging software at Gawker, and Nick has a lot to say about where it should be going. One thing he says should be easier is images.”…
Isn’t it easy already? Did you try BlogJet? It easy, very easy to insert images in your posts with BlogJet: as easy as in Microsoft Word.
If your blogging platform supports MetaWeblog’s API method to upload files, you already have this feature. If not, just configure your FTP server. And Flickr integration coming soon…
(Here’s a tip on how to configure BlogJet to post images to WordPress.com without using FTP).