The best option for me has always been to use ScriptRunner to do scripting in Jira. Simple to insert scripts, plenty of examples around, no need to learn new languages (my scripts are a mix of the Java I've learned while working with Jira and Groovy), plus there's loads of experts around to ask.
I accept that I will be accused of bias, as I work for Adaptavist, but I joined a year before they acquired ScriptRunner, and have been using SR a lot longer before that. I'd make the same recommendation if I didn't work there.
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