Apple doesn't allow iTunes to import music from an iPod because of a deal they made with the RIAA. If he were to just attach an iPod to a computer that it hasn't been synced with before, it will ask if he wants to erase everything and start over, which he of course doesn't want to do. Luckily, it's not difficult to get around this roadblock. Mike will need a program such as Sharepod. This will not only import all the music, but will also include playlists and album art.
Leo recommends using one of these services to keep his music backed up, although Leo actually uses both:
- iTunes Match
- Google Play (aka Google Music)
For an annual cost of $25, iTunes Match will save Mike's music to the cloud and upgrade them to 256kb AAC with no copy protection. While Apple doesn't use copy protection, it's important to note that they do embed the user's email address into the file. So if the file were to be distributed over the internet, everyone would know it was him. Mike only needs to buy one year's worth of service just to get the higher quality files. If he had songs that were really low quality, less than 96kb, iTunes Match won't do anything with it. There's a way around this too -- He can re-encode the songs at 128kb through iTunes, and then they'll be matched and stored in the cloud.
After iTunes has matched the songs, Mike can delete all the matched songs from his library and re-download them to get the higher quality copies. Macworld has some good articles to read about iTunes Match.
Google Play will upload his songs to the cloud for free.