Multiple file download ASP VB

Here's my problem. I want users to go to an ASP page with a bunch of links to files. The user will view the files as checkboxed items. Each file they want they will check off. Once they have all the files they need, click a button to popup a browse dialog of where to save these files on thier own (local) harddrive. Once they specify a path, download all the checked files to that folder, showing some kind of progress indicator for these.

Now I've got the ASP page all hacked out as to the files and how they will be checked off, what I need is the next step, the sending of multiple files to a remote drive and showing the progress of the download. Here's another wrench into the mix. Some of the files the user might want are located in ZIP files. If it's in a ZIP file, it must be extracted (server side) before being sent. Should I code something VB wise as an EXE or DLL, or do this all through ASP and script?

I need some advice on where I should start in this and maybe some good examples of how things like this may have been done before. This is relativly new territory for me but believe me, the help will be appreciated. Thanks in advance!

This is harder than I thought I guess. I'm not looking for specifics persay, just a direction I need to go. Maybe just some Psuedo code of how I can tackle this. Has anyone ever done this before?