Upgrading is going from one major version to the next. There is a higher risk of failure when doing so.
Updating is increasing the minor version, including bug fixes and small patches.
I am sure I was one of those people who upgraded their machine from 9.0.3 or 9.0.4 to 9.1, and I do not remember batting an eye doing so. By this time, updates were readily available via the Internet — this should have been a fairly straightforward process, without the need for CDs or multiple hard drives.