Update: Daniel at DisplayLink support replied to the log I sent.
I was instructed to do the following if the screen don't wake when I wake my laptop (running in clamshell mode):
1. Please download the DisplayLink Support Tool available here
3. Log into your computer (I can do this by simply opening the laptop)
4. Launch DisplayLink Support Tool.
5. Then select Advanced in the left top corner of your top menu bar and once expanded select Reset Screen Layout.
6. Display arrangement may need to be reconfigured in Mac settings.
Daniel did not say whether this actually solves the underlying problem.
I'll keep running this and see if it does.
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