As the geekiest soldier in the Central Band of the Royal Swedish Army Band 2008, I am responsible for the band's unofficial website: http://www.amk2008.se.
One thing I and others with me have found problematic is uploading images to the site. Formerly, I used standard html file upload controls to send the files one by one. But as it used to crash when sending large files and the process of uploading many files became quite a pain, I decided to code a client-server java + php & mysql solution.
It is my first real java application but is working quite well by now and I will publish it as open source when it soon will be ready for shipping.