There is a potential problem with this extension regarding “win32api.so”.
It is providing only one (1) “win32api.so” binary.
Which is it 32-bit or 64-bit ?
It really aught to load the binary from the Standard Ruby library distributed with SketchUp.
There are also several other binaries provided. If they run within SketchUp’s process they need to match SketchUp & Ruby bitness.