What your refering to is an all city meeting, and yes chicago has one about every two years from some one trying to relive upski's tales but testosterone, and ego's get in the way, fights break out and no one gets to paint.
Try saving your pictures in the correct format, i.e. jpg., then upload it.
instead of buying a program just get a free webspace, most of them are easy to use and make it even easier to upload pics.
-------signed a computer geek------------