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There is a known issue with the older transition exe's in the EnergyPlus v9-1-0 release. If you have an older version of EnergyPlus installed, use the binaries from there for any transition other than Transition-V8-9-0-to-V9-0-0.

However, from the error messages shown above, it appears that the transition program did not find the IDD files which reside in EnergyPlus-9-1-0/PreProcess/IDFVersionUpdater. Try moving to EnergyPlus-9-1-0/PreProcess/IDFVersionUpdater as the current working directory and execute transition from there. Or better yet to EnergyPlus-8-9-0... if you have that installed.