I believe the problem in your reasoning is assuming that the position/wave function of the object evolves in discrete intervals.
You state
subsequent measurements should find the object in the same position unless a significant time has elapsed allowing the wave function to re-expand?
This seems to imply that either a threshold of time elapsed needs to be reached for the wave function to evolve (and significantly, that threshold of time is larger than the Planck Time, so the theory still allows us to speak about changes within that time frame) or a threshold of wave function spread needs to be crossed for the position to be able to measured elsewhere.
However, QM gives us no reason to think so. The solutions of the Schroedinger equation (or any of the alternative QM equations we choose to use) evolve continuously over time. That is to say immediately after we measure an object in a definite position, the wave function will have already started spreading around that position. How much it spreads depends on how much time you wait, but it's not going to be zero no matter how small the timespan.
Given a wave function distributed over space, even if that space is very small, we can derive from the Born rule that there is a probability for the object to be measured in any position within that space. There's no rule that says the distribution needs to be large before the Born rule applies or before we can make a measurement.
Therefore, if we make a measurement every Planck time seconds, on the first measurement we will find the object on a definite position; on the second measurement, the wave function will have spread into a small volume around that position and we can measure the object anywhere within that volume. On the third measurement, the wave function will have spread a little in a volume around the second position and we can measure the object anywhere within that volume. There's no reason to assume that the three measured positions so far would align in a line, so it's likely they'll form an angle. Continuing like this, the repeated angles will form a zig-zag pattern.
Generally speaking we can't actually observe this zig-zag pattern (at least to my knowledge/on that scale), because our measurement equipment does not have the extreme accuracy required to measure such small distances. This is why it might look like the object isn't moving unless a significant amount of time does not pass (assuming an object with no momentum). However, the question hypothesised the possibility of being able to make a measurement every Planck time seconds, so I engaged with this hypothetical scenario where we have measurement equipment of perfect accuracy.