I just tested it briefly and it works here (using MeeCast version 0.9.3).
Are you using the latest SkippingStones version from the github repository (not from OpenRepos)?
Did you push the respective button in SkippingStones for enabling SmartStatus support (You need to scroll down a bit to see those buttons.)?
Are you using exactly those SmartStatus watch apps that are linked to here in this thread?
Are other SmartStatus features, e.g., MediaPlayer control or displaying phone battery status working in the SmartStatus watch apps?

By the way, the weather information on the watch is only updated when the MeeCast app cover is updated.
You could try to add another location and switch between locations and see what happens when the MeeCast app cover is updated.

Finally, please keep in mind that all this is very experimental and far from being stable.
There are many parts that need to play together nicely for all this to work, so things can break at many different places.
All contributions, code, testing, documentation, etc. are very much appreciated.