Basically, the Upgrade Assistant will shutdown your database, start it with the new software, and run an upgrade script. You can perform this task manually as well. The upgrade script takes the same amount of time (roughly) for a 60 GB database as a 600 GB database. The length of time for the upgrade script is not dependent on the size of the database.
I would highly recommend reading the Oracle 9i Migration Guide before migrating your database to a new version. It contains tons of details and information. Many migration headaches can disappear if you simply take time to read and understand this document before proceeding.
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