You are using server side code to upload files in postback. So, though you have controls within the loop, assigning a counter in a label will not display the changes until the whole operation done and the page is fully loaded.
So, you need something which you can interact from client side. So, Ajax is the first choice to cope up with this scenario.
Have a look to this link,
Simple AJAX File Upload[
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Hope this clears your confusion.
cheers