headcanon question time!
is there any person that joshua deeply regrets killing? not in the sense of 'i wish i didn't have to' or like that, but instead more along the lines of 'that was not needed' or 'this haunts me'?
Yes. In both main and FFVII, Joshua has a couple of murders that... keep him up at night.
In his main verse, there was an interrogation of a Dhalmekian merchant who had been trading in Rosarian relics. The man was not a good person, and had been complicit in aiding the black market trading and smuggling of ancient writings of the Phoenix, but that didn't mean he should lose his life. And he wasn't going to be killed, just shaken and roughed up by the Undying and released once they had gotten all the information they could from him.
It happened after the man admitting to throwing out, not even selling, a book that contained the histories of the prior Phoenix's. The book was never recovered and it's likely there wouldn't have been anything inside of it to help locate Ultima, but it was his family's history that was lost. Hearing about how casually the man had decided it would be worthless and had tossed it aside had Joshua seeing red for a moment.
The worst part of it was that he didn't feel much of anything at all afterward. There was no guilt, no I shouldn't have done that, not until Jote chastised him. In private, of course. The ramifications of what he had done and how easily he had done it sank in over the next several days. The man was awful, but he didn't deserve death, and Joshua killed him all the same without hesitation or a second thought.
In his FFVII verse, there was a mother fleeing with her children from the battle in Wutai. Joshua watched her run, getting almost out of sight, and then lit her on fire to burn her alive. One of the children might have escaped, but he knows one of them was caught in the fire as well.
She had been an unarmed civilian trying to flee for her life.
At the time, Joshua had thought he had simply been participating in a VR simulation, and he's not entirely sure if it was a simulation or, as the unnamed grunt who likely died for telling him this had said, actually real and he was being an idiot for believing it wasn't. It was real, and he committed some pretty awful war crimes that his mind refuses to really come to terms with.