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This "All In Order" challenge is also available for the Apartment Heists. Same thing, now a million dollar reward. The last 27 Apartment Heist missions you played have to follow the Top to Bottom order in the board, no exceptions, even when more than one are unlocked at a time. Same for the Doomsday Heists, but the reward can be disappointing in that one.
For Special Cargo, getting the Boat sale with Ghost Organization is also the safest, if i'm right! There's a speed upgrade you can buy for it in any of your Special Cargo Warehouses. Look for the giant mechanic's toolbox
1 - Casino - Loose Cheng (50k)
2 - Casino - House Keeping (50k)
3 - Casino - Strong Arm Tactics (50k)
4 - Casino - Play to Win (50k)
5 - Casino - Bad Beat (50k)
6 - Casino - Cashing Out (100k)
Only achieveable once. For example, don't lose a life in Strong Arm Tactics and you will earn 50k on top of the mission Award's 50k, but cannot be earned again in any other mission.
• Completing all of these as a Crew Member will earn you 100k.
• Completing all of these as a Host will earn you 100k and the Paragon R (Armored).
• Completing all of these in order, meaning have these six missions have to be the last Diamond Casino Penthouse missions you have played, from top to bottom from the list above, will earn you 500k.
Having all this in mind, you can earn up to 1 million in one playthrough, but these are all achievable one time per Game ownership, if i'm not mistaken, and if you buy a Penthouse to unlock these, you're really only getting a 1 million discount out of the 1.5 million base price.