If Five second guessed himself the moment they started to walk away, he doesn't let it show. Considering they're on a mission to murder someone, it's probably better this way. Allison can handle herself, and he's got a few reasons for keeping Wrath in his sights.

The poison is powerful enough that he asked for help, but he hasn't seen him display the weakness he says he feels. He even opts to walk there instead of teleporting, up until they get near.

He turns to him and seems surprised at his reasoning. It's true, it'll be easiest to get the job done if he bypasses any security, but he didn't expect bloodshed to be a concern when that's the entire point.

While he could question him and maybe learn a few things, they're on a deadline and he'd really like to get this murder out of the way. He looks to the house ahead, trying to spot any figures moving behind the windows. Five's ego whispers to him all the ways he could do this more efficiently on his own, and it contradicts any earlier feeling of relief that he didn't have to this time. At no point did he come because he wants to be a part of this.

"Which one is it?" Assuming he already knows exactly where this man spends his time. He'd ask how he's familiar with him, but maybe that's a question for after he's dead.