It still appears there is still a race between Hugo and Tailwind where classes are applied but the CSS is not (in fast render mode). I have to kill the server and restart it for the styles to be generated.
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This might be a more general issue with the generation of styles via PostCSS and the file watcher. I am experiencing the same problems with a Bootstrap-based project where changes are acknowledged, but the CSS is not created. Because I am not sure if that is an issue in my config or GoHugo I am just restarting the server for now 
Got the same thing going on.
I honestly just restart server reflexively.
It becomes tiresome though coz my site takes a minute or more to build, especially when several Tailwind classes are involved.