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DONT meet him only get robbed all the time and kill them
they will tell you to visit him
beat him first try and you should get it
both achivs
1. Start a new game, (get robbed obviously)
2.Carry money and get robbed
3. Beat all the muggers
4. Meet Bobo or whatever and fight him and win first try
Go for an agi build 1/8/4 you can get meat runner I and dont fall down II so you can stop going to the gym.
Dont do the fifth bar fight to unlock Micky. You can do 4 safely.
You don't need to beat/fight the mugger in Apu's to get crime fighter - I think he only appears if you get all 3 free meals off of Mick.
Do lots of pizza runs to get cash - feel free to fight the crocodiles.
When you have >150 dollars you can get mugged.
You can only get mugged every 4 days.
Once you have beaten all three muggers (Huey, Duey & Luey I think) you will unlock Crime Fighter and the trailer park where Bobo and Micky are.
You only get one shot to beat Bobo so if you lose you can't get the achievment that game.
So go to the gym and train your stats up a bit 1/10/5 or so.
Beat Bobo and get Triple B.
Most of the achievments are just for taking both routes through the story.
Only other "skipable" achievements are for beating all four crocodiles; the work for Bobo chain (sound of music & the mobster); and beating the game in 100 days.