I have been using WordPress for about five years. I have been uploading media the entire time and normally don't have issues. For some reason, the last few months I hvae noticed that my media uploads are just dragging. I make sure to optimize all my media before uploading (images less than 100kb, small images less than 50kb). Most recently the uploader choked on a 5kb thumbnail for a new post, twice. I finally got it to upload after about 5 minutes of waiting. I am not sure if this is a WordPress Glitch or a Hosting glitch.
http://www.ugmspokane.org is my site
I host with Dreamhost (they have been great to me - used them on all my wordpress installs)