If you use Kindlegen to create a MOBI file from a suite of files including an OPF and NCX file, the resulting MOBI file will incorporate the waypoints coded in the NCX file. It's still the case that Kindle won't recognise nested waypoints, but as long as you keep a "flat" structure in the NCX file, the Kindle will recognise the waypoints, and the 5-way control on the Kindle can be used to jump to the next/previous waypoint in the book.
I'm afraid I don't know what the current situation is regarding MOBI files created using Calibre.
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