You'll need some code to do that as I read it.
You can do "current user is the reporter and the current user is in group X" off-the-shelf.
But I think you're asking for "Check that the reporter of the issue, Chuck, is in group X, when Dave is trying to perform the transition", which is not an option you have.
I'd use the script runner for this, as usual, but there are other add-ons that support scripted conditions, and probably one that could provide exactly that condition.
It should be. I'm not a proper coder either, but I think you'll want something that can get the list of users in a group, and check if the issue.reporter is in the list.
I would say check for groups in issue.reporter.getGroups(), but there is easy getGroups() function and no way to directly read a user and say "what groups are they in" as far as I can make out.
I have multiple projects that use variations of the same base workflow. The variations depend on the requirements of the project or issue type. The variations mostly come in the form of new statuses ...
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