Okay, so I finally got DisplayLink 5.2.1 working with Catalina 10.15.2, after following all the directions and performing a bunch of installs/uninstalls (none of which worked...lol).
I have a Mac Mini (late 2012) and I was running High Sierra. I figured there would be some issues updating DisplayPort, after updating to Catalina (DisplayLink has historically,never been an easy install...that's why I always perform a backup before mucking up my machine). I have a 15" AOC monitor which has been getting its power from the USB ports on my Mac Mini.
Anyway, after updating to Catalina, I installed DisplayLink 5.2.1, allowed permission for the install, made sure that DisplayLink was enabled in the "Accessibility" control panel, made sure that it was enabled in "Screen Sharing", and made sure the extension was loaded in "About this Mac" | System Report | Software | Extensions.
After doing that several times (with no luck), I figured I'd try putting a powered USB 3.0 hub between the monitor and my Mac. That did the trick.
It seems that, perhaps, either Mac OS X Catalina or DisplayLink no longer consider the two onboard Mac USB ports sufficient enough to power the monitor.
That may or may not be your issue, but it's worth a shot (I believe newer MacBooks have USB-C and that specification is supposed to, theoretically, provide adequate power). The main downside is that you wouldn't be able to be free from being near an AC outlet.
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