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An update to my original question: I have Ruby 2.7.2 Installed and can run any of the Test scripts in the measures Github repo (openstudio-common-measures-gem-develop). Which is fine, I can also run any test from the OpenStudio CLI.
The ruby version seems critical, and has to be as per the OpenStudio version compatibility matrix in order for any of the measures to be run in an IDE.
However most IDE tools like VScode etc all assume ruby 3.x is installed.
Most of the debuggers and extensions for VScode (rdbg, lsp etc) wont work with Ruby 2.x.
IF you install a newer version of Ruby , then all of the OS measures scripts wont run as they fail the initial version checks.
Are there any plans to update OpenStudio to run on a newer version of Ruby. As it would be great to be able to take an existing measures script and run it in debug mode line by line?