A long time ago R@S gave me a good solution to this mission.
When you arrive in the city, kill the armed civillians(saiga shotguns),
those are his buddys.
Then just let time advance while on the map screen and you will get a battle note when he enters the sector. Just waste him then.
Its kind of a work around, but the mission is coded shoddy to begin with and just a pain to complete like the devs wanted you to.
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