This is the most time consuming achievement to get outside of the "Full Season" campaign. First off, you need to pick either Matthew or Nick (they both have 4 bars for the Patch ability). You need to go into a tournament, create a 2 player "Bonanza" and set the turn length to 8 days. Once that is done select PLAYER 2 and have them rest for the full 8 days time frame.
Now the fun part begins!
Pick the boat that has the worst reliability rating (You want it to break down!), fill up your gas tank to maximum, leave the dock and just drive from the farthest fishing point on the left to the farthest fishing point on the right side of the map and keep driving around doing this until you either break something that needs to be repaired or possibly run out of fuel. You are doing this so you can break the motor (or other item) on the boat.
Once its broken use either Matthew or Nick (only use 1 person the whole time for patching, don't use anyone else or your time will run out before the tournament is over) and patch the motor. Try to hit as many of the stars (a maximum of 6 or 7 stars will be available until you have a 5th bar patch ability) as your can. The time you take is irrevelant, hitting the stars will help you gain that 5th bar on the patch ability to enable the 8th star to show up. You will need to repair 3 things before either guys hits a 5th bar on the patch ability. Once they do just drive around until something else breaks and then use that crew member to fix the item for your achievement.