I have a similar problem, I'm on ArcMap 10.4. I have two types of points and two types of lines on my data-driven pages (DDP). The legend only shows the uppermost line on the TOC and the uppermost point on the TOC. I only have 6 DDP, but I will eventually have 166.
I tried the 'arcpy.RefreshActiveView()' with no change.
I could really use a GIS Jedi.
legend = arcpy.mapping.ListLayoutElements(mxd, "LEGEND_ELEMENT", "Legend") [0]
legend.adjustColumnCount(1)
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