Have you taken a look at NeatUpload? This module will allow you to upload
multiple files (as long as the combined size doesn't exceed 2Gig) as well as
be able to have a progress bar and the ability to cancel the upload. Also,
if you plan on uploading large files 100Megs and greater this module will be
much more efficient on the server memory because it goes in chunks. Unlike
the built-in file upload control where if you upload a 100 meg file the
server has to be able to allocate 100 megs of memory before it will fire its
event. Anyway, we use this module in a web app where I work and we can
easily upload multiple files up to 2 gig total per postback.