Switching from Windows 7 to Mac OS 10

Been there done that. First question - yes!. Go the Apple website and read Switcher 101. Lot's of good info. Second question - no. Once you have moved all your iTunes stuff to your Mac connect it. Since OSX cannot read NTFS (Windows file system) you will have to do a restore.

Enjoy.

FWIW, I moved to Apple hardware about 3 1/2 years ago and have not looked back.

Assuming the library is in the usual location on the PC and consolidated, i.e. all files are in the *C:\Users\<User>\Music\iTunes\iTunes Media* folder:

Copy the entire iTunes folder from the PC to the Mac. I.e. copy the folder C:Users<User>MusiciTunes from the PC to <User>/Music/iTunes on the Mac. If you've already setup iTunes on the Mac rename <User>/Music/iTunes as *<User>/Music/iTunes (Empty)* first. N.b. you can either network the computers or use a FAT32 formatted drive to handle the transfer.

On the Mac, rename the file *<User>/Music/iTunes/iTunes Library.itl* as *<User>/Music/iTunes/iTunes Library*.

Delete the files *iTunes Library Genius.itdb* (apparently the Mac & PC version are not compatible) and *iTunes (Music) Library.xml*. iTunes will rebuild them automatically.

Start iTunes. This is the same library you used before and your devices should sync to it as if nothing has happened, at least as far as the media is concerned. I've no personal experience with contacts and other PIM data as I'm synced with Exchange but (where applicable) it should remain on the device and you should be able to set it up to sync with your new computer.

tt2

Since OSX cannot read NTFS (Windows file system) you will have to do a restore.

Actually, Mac OS read NTFS quite well.
It cannot write to it (without using a 3rd party app).
But yes, the iPod should be restored on the Mac.