The angle the point is at in relation to the angle of the wheel will be constant if it is attached. To see if it falls within a certain range, mod it and see!
EDIT: Oh, I see there are a couple of gotchas, namely that positive roll rotations seem to turn entities negatively and that EntityRoll() can actually be a negative. Here's a (long-winded!) solution...
The trick is to get the point's global angle within the normal 0-359 degree range and then specify that you are checking it against values supplied in a clockwise direction (although, of course, you could just as easily go with anticlockwise as long as you pick one and stick to it, but that's more typing!) That way you can tell which portion to check and whether it transcends zero.
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