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Is one preferred over the other? If so, in all cases or just a few?
I am intending to use some form of date class for keeping long lists of date and time data, e.g. '2009-01-01 10:12:00'.
struct_time is the old way of representing times, modeled after the C standard library. datetime came later, is more pythonic, is more featureful, and has more predictable behavior in edge cases than the struct_time functions. I would use datetime except in the rare cases where a measured performance difference is significant enough to matter, or where it makes the code significantly less readable.