Does ipywidgets support multiple button clicks?

The short answer is ‘yes’.
Example:
go here and launch a session and then choose from the available notebooks ‘3D scatter plot using data in a file and Voila interface’. Run that cell as a notebook and you’ll see it offers to upload and the plot. You can upload a different .tsv and click the ‘Plot Selected’ button again and it will try to plot the data. It will probably error because it won’t match the field expected; however, it does work. You can prove that by switching to the lab interface and downloading the wines_from_winequality.tsv file to your machine renaming it (,you could even alter some of the data to really test,) and then uploading that renamed file to the system. Then hit ‘Plot Selected’ again and it will plot that data just fine.

However, I suspect you are getting at something larger than this maybe? I wouldn’t know it from your current example you proffered though. Anyway…
if you need to monitor something after you click the button, see replies here where a timer function is built into one button. That thread will also lead here where various options are offered, like asyncio. (Shout out to more aysncio with ipywdigets magic here.)