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If you took advantage of Flight School at Los Santos International Airport, you'll probably remember a move called a "knife". For those that forgot or don't know, a knife is when you are piloting an airplane and roll to one side so that the aircraft is sideways with the wings vertical. Control is kept by using the rudder or yaw (normal side-to-side) to maintain altitude and adjusting pitch (normal up/down) to keep the airplane moving straight.
There are 15 locations around Los Santos which task you with doing a knife flight between buildings (Note: only 8 are needed for 100% but all 15 are needed for the trophy/achievement). Not every opening you see is one of these and a couple you would probably never notice. Below is a general map of the locations:
Now here's a closer look at each using a satellite image of the city. For most of these you can approach from either end but a few are better when approached from a certain side due to nearby obstacles. Click the screenshot for a larger size.
1. Pacific Bluffs
Sneak between the two hotel towers. Look out for the trees along the west.
2-3. Del Perro
A difficult and tight two-fer. Roll so you're cockpit is to the northeast which makes for an easier turn through.
4. Rockford Hills
This one sucks. You need to dip down low and get through the alley. Watch out for the movie studio to the south and hotel to the north. Both are tall.
5. Rockford Hills
Much easier than the previous. Fly between the two towers.
6. Little Seoul
A tight squeeze between the two twin buildings. Be careful of the other buildings to the south.
7-10. Pillbox Hill
Two easy sets between the four buildings. You should be able to get two each direction in one go.
11. Pillbox Hill
Simply pass between the FIB and IAA headquarter buildings.
12. Downtown Vinewood
Not much headroom here. Zip through the upper floors of these buildings just above a shorter rooftop on the south corner.
13. Downtown Vinewood
Squeeze between these two buildings. Watch out for the theater to the north.
14-15. West Vinewood
Two easy ones next to each other.
The Mallard (stunt plane) is the optimal choice for knife flights. It is steady and agile without being too fast or sensitive (like the P-996 Lazer).
It is a very good idea to use a character with maximum flying skills (such as Trevor).
You may wish to have Franklin or Michael purchase a hanger at LSX and store a Mallard there. This way you can easily get back to task after a crash since Trevor's airfield is a little further away. If you don't mind loading times or want to have a "perfect" save file without deaths you can also quick save before each attempt.
Line up your flight path a good distance away from the target and don't roll your airplane until needed.
Try to be level or pointed slightly upward when you perform the knife. This way your airplane will not head towards the ground (or lower obstacles) and crash. The rudder of the aircraft can only hold you steady and will not give you much lift during the knife.
Your airplane does not need to be in a perfect knife to make the objective but you need to be reasonably close.
Your flight path doesn't need to be straight through the buildings. Just get through.
Note: Even if you crash after going through the buildings, listen for the objective complete sound or check your stats (Pause menu > Stats > Vehicle) after respawn. Again, as long as you get through the buildings you should be good.