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It is really your decision!
The development model for Calibre is that Kovid (or others) make a change, and then do basic testing before releasing it for more general consumption. That means that any new release has only had basic testing before releasing (thus increasin the chance of a bug in a new feature or a regression in an existing one). On the other hand it does make for very fast turn-around if bugs are discovered.
This means that one level end users are the real serious testers and the developers are not tied up in large testing cycles. With calibre being multi-platform comprehensive testing would be extremely time consuming. The big benefit is extremely rapid incorporation of bug fixes, enhancements and new features. It is this model that has lead to the speed at which calibre is taken forward and improved.
If you do not want to always be in at the cutting edge, then probably the best thing is to read the change logs for each release to see if there is anything in there that is really important for you. If not, then you can consider just upgrading every so often.
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