EMPLOYER: Dom
PREREQUISITES: MM #47 (Predator), Must be Franklin
REWARDS/UNLOCKS: N/A
COMPLETION REQS:
1. Dare Devil: Fall for 8 seconds before opening the parachute.
2. Bullseye: Land perfectly on the back of the truck.
This one actually gave us some trouble!
First of all, you should know that Dom is already on top of the Maze Bank building and you have to meet him up there. You can't get up there without air support though, so you'll need a helicopter. Remember that you can easily steal a helicopter from the downtown emergency center (intersection of Crusade Road and Capital Blvd). The top of the bank has a nice big helipad so landing should be easy.
Once you meet Dom you'll get into a parachute outfit automatically. Now, this jump isn't so simple as "survive": you actually have to land on the back of a flat-bed truck driving downtown (if you don't land on the bed the mission will fail). This can be a little tricky but thankfully we've done this several times and got a good strategy.
First follow Dom and jump off the building. Now you want to wait for about 10 seconds (count to 10 to yourself) and deploy the parachute. The game will notify you of the truck by the time you deploy. Thanks to the time you gave yourself, you'll not only have the "Dare Devil" medal requirement down but you'll also have a perfect opportunity to line yourself up with the truck.
Press R1 and L1 and get in the same lane as the truck and descend naturally. It will look like you are in front of the truck and you are going to overshoot it: this is natural. It will catch up with you soon. In fact you may have to press down on the analog stick when you are close to it to ensure you hit the bed. Either way, with your 10 second drop you should be able to line yourself up with the trunk (and the lane it is in) and descend down to it deliberately.
Once you've done that watch the rest of the scenes.
If I wait 10 seconds I hit the ground. That's really bad advice.