Resolved - dead Targus
Connected my laptop to a friends Targus hub and the displayport worked great. Took my friends laptop and connected it to my device... same results - the displayport was not recognized.
At this point, I think it is safe to conclude that it is not a software issue on the laptop, but a software (or hardware) failure on the displayport. It's been working fine for years, so I am surprised that it just died without any indication of pending problems.
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