EDIT: Thanks to everyone commenting with additional information.
EDIT: This achievement is partially unobtainable now due to Rockstar removing the parachuting and sea races. They have said they will rotate jobs in and out, so it would be recommended to jump on these jobs if they do reappear again. Also, the Xbox 360 servers shut on 16th December. Good luck to all who still need it.
After attempting this achievement numerous ways, my friends and I figured out that this is mostly linked to the Victory Awards which can be found via pausing the online, going to stats, and clicking Awards. After clicking Victory, you will be able to see which medals which you have and haven't progressed.
These can be boosted in closed sessions with friends, most can be done with 2 players, with a few requiring 4. It has been confirmed by some gamers now that doing races solo does not count towards this achievement.Here is a list of the awards which are required.
(These must be wins, draws/everyone else getting DNF do not count)- Win a Deathmatch
- Win a Team Deathmatch
Requires 3 or more players, doesn't include Last Team Standing. (Rank 6 gives access to the Supply TDM at Cypress Flats, which is 3-6.
UPDATE: You can do TDM with 2 people by starting a regular deathmatch that requires 2 people, then switch it to TDM.)
- Win a Land Race
- Win an Air Race
- Win a Sea Race
- Win a GTA Race (To do a GTA Race, the host of the race must switch it from a standard race to GTA)
- Win a Rally Race (The host of the race must select Rally as the race type)
Requires more than 2 players- Win at Arm Wrestling
- Win at Darts
- Win a round of Golf (Can be set to 1 hole)
- Win at Tennis (Can be a single Set)
- Complete all Waves of Survival (Some say you have to survive all 10 waves, whereas others say it unlocked after completing it, regardless of deaths.)
- Win any challenge at the Shooting Range
(Edit on 28th Oct) To help clear up some confusion, this has to be the challenge, not just a round. If you set it to one challenge, you must win 2 out of 3 rounds.
Game Types which aren't covered by the Victory Awards which are also required include:
- Parachuting (If the other players all get a DNF, the win will not count)
- Gang Attack
(Must be done with another player taking part in the attack)Some people have only had their achievements unlock after completing a mission, so the completion of any mission may be needed too.
EDIT:Supaduparich pointed the following out in the comments, which could explain why some people are struggling with this achievement.
Just want to add the stat tracking for parachuting is bugged. If you are having trouble unlocking this check your social club win stats and see which one is still at 0. I had a friend leap to their death and I got points. I won the event and achievement popped.
Survival tips- It helps to use a map where you and your team can hold position. The Boneyard has a big building with two entrances and is a good choice for four players, with two on each entrance.
-Another good map is Processed, you can hide in the middle hanger behind the sandbags, with two other players behind the small cabin inside there. Be careful as some enemies climb over the fence, but aside that, it is an easier map.
-If you have leveled up enough, you can call in Merryweather support. Backup helicopters, ammo drops, mercenaries and airstrikes can turn things around if you are struggling.
Edit after patch 1.04The rooftop on Boneyard is now off limits, as is the store in Sandy Shores. The Sawmill can be done with two people if you hide inside of it, it is a slower process but mostly safe.
Disclaimer Please note that sometimes progress can be lost due to the Rockstar Cloud services not working, so if you feel you have done all of these, check the award progress to make sure that it has stored the progress.