Q: Syncing Original iPod to Laptop

Ideally, you should restore your complete iTunes data (including your library file and all media flies), instead of offloading only song files from an iPod.  This is better, because you get the same iTunes library (with supporting data such as playlists, ratings, play count, data added, etc.) on the new Windows installation.  If you can do this, because you have a data backup from before the "factory reset" of your laptop, please post back for more info.

Otherwise, you cannot use iTunes to transfer song files from iPod to computer (except for songs purchased from iTunes Store).  By design, iTunes syncing is generally in one direction only, from iTunes library to iPod.  However, there are third-party methods and utilities that can transfer from iPod to computer.  If you do an Internet search on something like "ipod music transfer," you should get some useful links, including an article by CNET on the topic.

After your songs files from iPod are on your computer's drive, add them to your new iTunes library.  When your iTunes library is complete, you can sync the iPod to it.  Your iPod is initially erase, but is reloaded from your new iTunes library.

iPad?  Why don't you just do that search and see what you get...