James,
You could either use the desktop tools or the ArcPad Server Extension to check out data from an Oracle database.
It all depends on your level of knowledge which road you should take. My suggestion, for new ArcPad users, would be to stick with the desktop tools. Once you're more comfortable with the workflow, and if you feel that the server synchronization would benefit your organization, you could give the server extension a try.
Feel free to respond with additional questions related to these workflows.