The answer accepted here (JFreechart(Java) - How to draw lines that is partially dashed lines and partially solid lines?) helped me start down the path of changing my series
I'm still having the same problem of the line not changing from solid to dashed, but being one or the other.
The setDrawSeriesLineAsPath() method "controls whether or not each series is drawn as a single path." This precludes changing the Stroke dynamically, as getItemStroke() will be called only once per series.
Addendum: An easy way to verify this is to invoke setDrawSeriesLineAsPath() in @GrahamA's example and break in drawFirstPassShape() in the debugger.