There can be no LoadError, unless the extension is installed. If the version displayed for the Trimble Connect extension, in the Window > Preferences > Extensions, is the latest, then the update should have been successful.
If the library file could not be found, there would be a different error message displayed for the LoadError. Ie:
require 'GoofBallNoFile.so'
Error: #<LoadError: cannot load such file -- GoofBallNoFile.so>
The “127: The specified procedure could not be found.” message indicates Ruby cannot find the entry point function, it expects to find IN the library file.
The error message (although cryptic) sometimes happens when the wrong bitness so library file is trying to load. (It has happened in previous cycles that the deployed packages had the wrong compiled binary so in them, and they had to re-release the extension.)
But it also happens when the entry point function is not named correctly.
Other than what we’ve tried, you could check that you have read and write permissions on all folders from the appdata “Plugins” on down, and the program files “SketchUp 2016/ShippedExtensions” on down.
Make sure SketchUp is set to run in administrator mode. (Right-click the icon, Properties, switch to Compatibility panel, check the box under Privilege Level.)