...if you are on peer-to-peer, you probably don't have to do anything (unless your main computer is running XP, and then you take it to 7). You may need a service pack for your Win7 main machine.
It's about the same. Only have to do something if you're on Server 2003 or lower. (Came out the same time as XP.) If they are still running Server 2003, they obviously got their money's worth with 10 years of usability. If you're on Server 2008/Vista, just need Service Pack 2. In fact, they are bundled under the same download.
What's complicated in this case is that Ted needs to migrate 20 Users with full email, Medware, etc. Many features that aren't available on Windows 7/P2P. Also I think 20 Users/devices is the limit for Windows 7 Pro. He's definitely out of the the P2P zone. Managing 20 user accounts separately on each computer isn't something that's worthwhile. This is where Active Directory is much better.