I've written a shuffle operator that can randomize the order of a list.  
It's available here:  https://mklauber.github.io/tw5-plugins/

To use it in that way, you'd probably want something along the lines of 

<$list filter="[tag[Tag]shuffle[]first[]]">
<$action-navigate $to=<<currentTiddler>> />

On Monday, February 19, 2018 at 9:10:23 PM UTC-5, passingby wrote:
> Can anybody suggest a way to have a button which opens a random tiddler 
> out of all the tiddlers tagged with a particular tag?

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