All posts about that achievement are from 2016, almost one decade ago... I think it must be bugged. I'm finishing the game for the second time to complete the Don route and I haven't been attacked at street even once, and I'm carrying lot of money...

My training scores have to be below 15, and it'll take a while for the clubs to arrive. My English isn't the best, and you have to play at least on normal.

I`ve just completed the game 100% with all achievements, so it's not bugged you can get them too! Just make a new game to do it and you're right, don't go too fast, you have to walk with more than 150 dollars, and wait 4/5 days before thugs try to rob you again. I can't explain it very well in a few words, but check this guide, it helped me a lot!

https://steamhost.cn/steamcommunity_com/sharedfiles/filedetails/?id=645381933