ListView with LayoutTemplate and InsertItemTemplate

I have a couple of questions:
First, I have a UserControl that will employ either an AsyncFileUpload or a FileUpload (I haven't decided yet) in various places in a site. I want to use one control so that I have an "all-in-one-place" control for a consistent look/feel/functionality throughout the whole site.
On one particular page, I would like to use this user control in the InsertItemTemplate of a ListView, with an AJAX ModalPopupExtender. In other words, whatever result comes from the file upload control will be the value to be uploaded to the database. Are there any opinions, pro or con, on doing this?
Second, I want the above upload function to be activated by a button contained in the LayoutTemplate. The button just looks best in that area of the page (although, if worst came to worst, I could actually put the "Add Your Photo" button before the ListView control). However, in trying to accomplish ...