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Both of these are perfectly logical ways of thinking about it, yet the have different answers. So which is right?
The second method is not logical because it fails to take the fact that the tortoise and rabbit are moving at different paces and the distances are finite. Obviously it's untrue because something is capable of passing another thing, it's a little harder to disprove though as it serves as an illusion to how human brains tend to grasp logic.
This'd best be done by using measureable distances. Let's say that the tortoise is moving at 5kph and the rabbit is moving at 10kph. The rabbit starts off 5 meters behind the tortoise.
Once the tortoise has moved 2 meters, the rabbit has moved 4. Now the rabbit is 3 meters behind the tortoise. If the tortoise moves 1 meter, the rabbit will move 2 meters in that same amount of time. The rabbit is now 2 meters behind the tortoise. The tortoise can then move 50 decimeters and the rabbit will move one meter. The rabbit is now 1.5 meters behind the tortoise.
The problem is that things don't move in a set of fixed frames so to speak. If we take this example to larger distances, then we see it is inaccurate and not viable for representing how the tortoise and the rabbit move respective of each other. If the rabbit starts 5 meters behind the tortoise and moves 15 meters, the tortoise will have moved 7.5 meters and therefore, the rabbit is 2.5 meters ahead of the tortoise.
To make this simple, let's say the tortoise moves 1 meter per second (it's bloody desperate for exercise) and the rabbit moves at 2 meters per second (The rabbit is still 5 meters behind the tortoise). If the tortoise moves one meter, it took one second to do so, and it took one second for the rabbit to gain a meter on it (four meters behind it). If the tortoise moves 50 decimeters, it will have taken .5 seconds for that to happen, and the same amount of time for the rabbit to gain 50 decimeters, or move one meter (now at 3.5 meters behind the tortoise). This will contue with time being broken up into smaller and smaller segments. The time measurement will become 1 second, then 1.5 seconds, then 1.75 seconds, then 1.825 seconds, end continue. Never will it exceed seconds if the added distance (and the therefore the added time) is halved.
With these speeds, it will take 5 seconds for the rabbit to catch up with the tortoise. Therefore, the above example shows that the rabbit will never catch up to the tortoise in 2 seconds, not that it will never catch up.
If we change the distance the rabbit is behind the tortoise to 1 meter, then the scenario sort of works. As the tortoise moves one meter, the rabbit moves two and they're both in the same spot. It only takes one second for the rabbit to catch up, therefore the rabbit manages to catch up despite the limitation of halved distance with halved time imposed on the scenario.
Because of this, the idea of halving the distance travelled only adds uneccesary limitations to the problem and prevents it from being correct if the time it takes for the rabbit to catch up to the tortoise is 2 or more of whatever unjit of time you are using.
Upon looking back, I noticed you used a turtle instead of a tortoise. Just pretend I used turtle instead of tortoise, it's not really relevant.