Use modulo arithmetic.
// Pseudo-code
// error
error = (setPoint + 512 - currPos) % 1024 - 512;
This code shifts the setpoint from {0 .. 1023} to {512 .. 1535}, subtracts the actual position and gets the modulus. The answer will be in the range 0 - 1023 but will have a positive offset of 512 which is subtracted out. The resultant error will be in the range {-512 .. 511}.
Suppose my current position is 10 and setpoint is 1023. The error is 1023 - 10 = 1013 ...
error = (setPoint + 512 - currPos) % 1024 - 512;
// Calculation
error = (1023 + 512 - 10) % 1024 - 512
= 1525 % 1024 - 512
= 501 - 512
= -11
Update 1.
It seems that you want the geared output to run from 0° to 360° but that the assembly could overshoot slightly at 360° and, I presume, at 0°. The only way to handle this with your proportional control is to convert your encoder in software into a multi-turn encoder. This means keeping track of your revolutions and allowing your "total" value to run from, say, -90° to +450°.
Figure 1. Flowchart for 0° transition testing.