Hi,
[Sketchup (14) offers customizing the toolbar also for third party features.]
Unfortunately the arrangements don’t last. After restarting the application only the customization of Sketchup features reappear.
I’m working with an iMac under OS 10.8.5.
Installation of Plugins by automatic install via SketchUcation.
There is no floating Toolbar ether (in my special case: for Extrusion Tools).
There is a long-recognized startup issue in SketchUp on the Mac that causes the toolbar in the initial window to contain only default built-in tools. Your customized toolbar should appear if you close the initial window and open a new one. The problem occurs because Mac OS determinedly opens the window before SketchUp has processed your Ruby plugins and extensions. So far as I know, there is no other workaround.