Justin,
Most timeout problems are apache configuration, and I'd recommend not uploading files over a certain size via the web anyways. The issue becomes more "User" and less "programming" after awhile. People do not wait. You can flash a giant blinking orb with sounds saying "PLEASE WAIT WHILE THE FILE UPLOADS" and you will still get people canceling the upload because they are sick of waiting

BTW CGI::Ajax is a nice module to use if you haven't checked it out. Also if they are uploading images, once thing you can look at is a Java or ActiveX control that allows them to paste the clipboard to the web portal. This gives you the option to set how much compression the image gets and cut down the upload option. (I've used an ActiveX control called Online Image Editor for years and it sends data to the server using Base64).

If this does not help you at all, then hopefully it will give someone else some ideas. --