That is player knowledge, not character knowledge. Your character sees themself alone versus Benny with 15 thugs around him, after passing through a checkpoint where they take away all your decent weapons. It makes no roleplay sense to go after Benny unless you've got backup and/or enough hardware that you can just kick in the door and murder everybody.
I still maintain any guy who needs to capture you with a group of people is nothing, as a player or playing the character. I played my character through and through. Especially with it being my first playthrough of the game. I didn't know Benny would be easy, I figured he would've put up a fight. However, playing through having ED-E and Veronica, I found them both to be strong and easily able to take out their own share of monsters, so why not thugs? I spent the game leveling, getting stronger, and exploring to find better stuff so I could go burn Benny to the ground. My entire experience for the game was actually do get my revenge on Benny, and I did. Unfortunately, I am now bored of the game since my main reason to play the game, was to kill that son of a [censored]. And I did, and I still maintain it's the best feeling i'v had in a video game in along time.
As for the Checkpoint, I didn't go in planning to surrender Weapons. I went in to torch and kill everything in the Casino because I wanted Benny to be [censored] out of luck and ruin his business. Fortunately, the son of a [censored] was there to kill as well.