I've had a Contour GPS since they came out and have had to do several firmware upgrades during the time I've owned the cam. The software Contour provides automatically detects if you need an upgrade. My cam works great, the video is awesome, but I have actually not taken any stills so can't comment on that.
The Water proof case did take a while to come out but I use my cam for skiing and biking mostly so don't need the case for under water use although this summer I'll get one for Supping.
The new connect view bluetooth app is really cool too although it did have some bugs initially but had been working fine since the last firmware upgrade.