It depends. Recently, one of my favourite plugins broke so I've waited for the new Calibre that the updated plugin would work with. Sometimes, I just check what's new and decide whether I need it or not.
I've noticed that the more time I spend here on the forum, the more frequently I update Calibre

. I just find out sooner about changes, improvements etc. and want to check them and benefit from the latest developments

. When I'm not on the forum, I don't usually update Calibre (I don't react to the prompts in the application).
As I tend to spend a lot of time on the forum for some time and than not to visit it for a couple of days or weeks, depending on my mood and the time I have, the frequency of my updates varies heavily

.