A time delay is related to speed and distance. The further away something is, and the slower something travels, the longer it takes to reach a destination. Light takes 8.3 minutes to reach the Earth from the Sun, for instance, so there will always be a delay of 8.3 minutes as long as the distance from the Earth to the Sun remains constant, regardless of the time of year.
If Gravity traveled at the same slow speed as Light, then it would experience that same delay, again, regardless of the time of year. Moreover, if Gravity was that slow, then planets would orbit around their percieved Sun (67,728 miles off-center-plane from the actual Sun in the case of the Earth, and progressively further off-center-plane for planets in more remote orbits).
That is, if Gravity was as slow as Light.
On the other hand, if Gravity was subtantially faster than Light, then one would expect far less planer orbital deviation from the actual center-plane of the Sun. In fact, one would expect the horizontal-orbiting planets to roughly line up in the same orbital plane as each other.
Calculations for the perihelion of mercury, the advance of the moon's orbit from the tides all use gravity as propagating with c and they are accurate (though it may not be the cause).
Yes, there is always a delay, however if the common motion of the earth and sun affect the gravity or light path, twice a year the apparent position of the sun would be correct as the path is in line with the common motion.