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FextraBot

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Pretty sure you don't get Groundbreaker rep(+17) if you use persuasion.
if you are talking about Jessie's quest, i tried both option and got same amount of Groundbreaker rep ( in my case it was +15). So it looks like it doesnt matter if you pay him or persuade him.
You can also kill him and the three guards. The two outside stay friendly.
There is no option to negotiate down her debits with the "emotional anguish line".