Hey Doug,
Also, the file and assembly versions on the EXE show the initially installed version, also. Is this by design or am I doing something wrong?
Did you compile the updates with updated version numbers? wyUpdate doesn't change the version numbers of your compiled assemblies, you're responsible for that. So, change the version numbers and recompile your exes.
However, when I check the currently installed version through Add/Remove Programs, it still shows the initial release version, even after an update.
You need to do a little bit of registry editing: simply change the "DisplayVersion" value to the latest version.
HKLM\SOFTWARE\Microsoft\Windows\CurrentVersion\Uninstall\YourAppName
Also, to save time, you can use the %version% variable and every new version you create will use correct version (instead of having to type it each time you release a new version).
Tell me if this helps.