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Do you have any reason to upgrade to 5.5?

Many people still use 5.1 because that is already a complete language that works fine. Most people don't really need the new features. Plus if you stay on 5.1 you get compatibility with LuaJit and Luau so much better performance.

There are nice new features in recent updates, but so far our strategy has been to stick to the version we use.

You're probably better off finding a way to support both.

You typically don't update Lua, you pick a version and stick with it.

Is transpilation a thing in the Lua world like it is for JavaScript?

Like https://moonscript.org/ or https://teal-language.org/ ?