I know we're having fun and all with Ratblaster's devils advocate, but no matter what twist you throw into this, he has a right to be stupid. That's all.
Even then, the surviving perp collaborated EVERYTHING that happened on his end-- They saw the guy jogging, planned the hit and failed to execute. You can come up with conspiracy theories for the jogger all day long, but after that confession, his reasons for being out at night with $900 in cash jogging around no longer matter. They initiated the encounter. Admitted to it. Even the potentially biased story reports it that way. 'A' is not connected to 'B'. End of story. Literally.
And if you want devils advocate thrown right back at you, you have to take perp #2's word for it that he is telling the truth in saying the jogger said "you want to play games," since the report provides no corroboration as to any other source but the perps, a known brigand. This is after hostilities have been initiated by both perps anyway, so what he said and what he didn't say is also irrelevant.
This silliness of trying to find fault with the shooter through a charade of devils advocate is exactly that-- Silliness. "But he had $900 in his pocket!" Irrelevant given the surviving perp's own testimony as to the events and the subsequent deployment of the jogger's firearm. He might have an obsession with always carrying cash in case of the Apocalypse. As somebody else mentioned, he might not have trusted his roomie. He could have been off to see a hooker. Did they make him suddenly less justified in pulling his gun upon being attacked?
No.
Are we done now?