Money Cup Master
Win the Maloof NY contest
This is the first Maloof challenge available and is called "Maloof Money Cup NY". This is an easy challenge. It will be you against 5 other people. Coming in first in any of the 3 rounds will net you 5 points, 2nd nets 4 points, 3rd nets 3 points, 4th nets 2 points, and 5th nets 1 point. Last does not get you any points. The 3 rounds consist of: Best Grind Trick, Best trick down the center, and finally, a Jam. To get first at the end you must have the most points so I recommend ending as many of the rounds in first as possible. You should still take home the gold if you get 1st, 1st, 2nd or even 1st, 2nd, 2nd. Anything other than those is running it close so I recommend trying hard to get 1st in each round which isn't really that hard. Once you complete this you will unlock the Maloof NY Photo challenge.
Maloof Street Slayer
Complete the Maloof NY street OTL
For this one you have to complete the Own The Lot challenge called "Maloof Money Cup NY". For this own the lot there is 1 accumulation challenge, 2 Gap Challenges, 1 Tag the Spot, 1 solo shot challenge, and 1 trick list. It is pretty easy overall. Once you have completed all of the challenges for the own the lot the trophy will unlock.
Maloof Tranny Monster
Complete the Maloof NY Tranny OTL
To get this you will need to complete a list of tasks under the Own The Lot challenge "Maloof Secret Tranny Park". There is one accumulation challenge, 2 gap challenges, 1 tag the spot, 1 solo shot challenge, and 1 trick list. Once you complete this and grab yourself a nice silver trophy be sure to grab the second OTS location located in the secret skate park.
Picture Worth a Thousand Curbs
Complete both Maloof NY photo challenges
This has only 2 photo challenges for you to complete. Once you have completed both challenges the trophy will unlock. The two challenges are simple to own but take a bit more skill in order to kill. First challenge is "Clean up sheet". To own this one you have to grab over the garbage and dumpster, but to kill it you have to do a nollie 180 to fingerflip. You can only squeeze in two pumps, which is good enough. I recommend trying to kill the challenge. Once you beat that photo challenge the second one will open up which is right near an OTS location. The second challenge is called "Money Manual". To own this challenge you have to simply manual the hubba, but to kill the challenge you will have to nose manual and revert to a fakieflip off the hubba. There is a ramp a short distance to the right which you will probably need to use. Place the ramp a short distance from hubba to make it easier. You can either manual the hubba or, if you are a bit better at this type of game, simply land in a nose manual and spin the L/S 180 degrees from either left to right or right to left to do a revert near the end of the hubba and as soon as the revert is complete you will lose a lot of speed so I recommend going straight into the flip trick. This unlocks the trophy and the Maloof NY OTL.
Where's My Money?
Complete both Maloof NY OTS challenges
There are only two spots to own in the DLC and they aren't hard to find at all. They are both noted previously in the guide but the first one is near the second film challenge on the left and the second one is located in the secret tranny park. Both scores to own them are 900 points each but to kill them you must beat 1200 points. Once you own or kill both of these spots the trophy will unlock for you.