You can add new items to the DataView as well as calling the Udpate of the dataAdapter (or an Update statement to a ExecutNonQuery of the Command object)
As simple as uploading the aspx, dll and config files to the server.
If you want to develop on the server in real-time they need to support Front Page extensions.
Sorry I misunderstood your question.
I would put a bunch of OrElse together and list the types (jpg,gif, bmp, etc)
For example, I wouldn't allow PCX format. (but that's just me)
*Thinking out loud here*
Perharps create only 10 sets of radibuttonlists, (one for each category) once the user answers the first question from each category (1 to 10) then Postback (click a button) and you then use the same list to display the next set (11 to 20).