This can be earned after chapter 7 as this is when you unlock the advanced upgrade. If you use the Jefferson Provincial (The first car you steal in the game which becomes "your car") you only have to do 2 upgrades. If you use other cars some will require 3 upgrades for the achievement which isnt a big deal you will just need a little more money. If you use the Jefferson you will only need $1,043. Upgrade 1- $416 Upgrade 2- $627