My biggest pain point when trying new software is poor error messages, and without a community of people to help it's difficult to debug. To give a reverse situation, a client of mine was using Ruby 1.8.7p375 long after it was discontinued, but the documentation online and StackOverflow comments still helped me navigate through it. Well known bugs and limitations were clearly documented, supporting gems (which were not many) etc.. were all easily findable online, which is something I cannot easily say for new bleeding edge software.
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