What difference does which kind of land you pay with make?

Question

According to halacha, a damager must pay with the best land, a debtor must pay with middling land, and a person who owes a ketubah may pay with the worst land.

But I don't understand why it matters which kind of land you pay with. If the land is worth the value of the debt it doesn't matter what kind of land it is.

I've heard from others that the reason for the difference is convenience: it's cheaper to hire workers to plow 1 acre of good land than to hire workers to plow 10 acres of bad land. But shouldn't the expected expense of farming the land factor into its value? Presumably, a given parcel of good land costing the same as bad land would produce less crops because of the difference in salaries. So it's not clear to me why this makes any difference.

Answer 1

A few days ago I wrote:

In an agrarian society, it hurts more to lose a really nice piece of land, even if your rational brain knows it's worth just as much as that bigger piece of land you still own. Which will teach you a lesson next time to be more careful with your cattle. (I.e. think about it from the tortfeasor's perspective.)

In a similar vein, Rabbi Shlomo Zuckier published an essay with a nod to modern studies of behavioral economics.

While this is true from the perspective of classical economics, one might argue that, behaviorally, people would generally prefer to have the higher quality item over a similarly priced item of lower quality. This is for the simple reason that people enjoy having something of higher quality, even if its objective value is equivalent. As some scholars put it, “the consumer’s sense of gain or loss is directly related to the usefulness of the goods in question”; ... it can thus be argued that the item that is subjectively valued at a higher level will generate the greatest loss aversion, regardless of its objective value.

...And in assessing what would be a more severe punishment for the tortfeasor, imposing the penalty that damager pay from iddit is indeed more powerful, but on a psychological basis rather than an objective financial one.

Answer 2

A very good question. It seems from different Sugyot (Kiddushin, BM and more) that a $1000 worth of good land is perceivably worth more than $1000 worth of worst land. For example, אחים שחלקו - brothers that inherited land and seemingly divide it by its value might have additional considerations, not strictly assessable in value and therefore they are allowed to break the deal later.

A possible reason for that is (my own conclusion) that in their times they had very little flexibility in prices, and the price did not reflect additional considerations. This is consistent with the Sugya of Ona'a - how come that different tomato are sold in the market for the same price? So they had a price list with only 3 types of land, however, the "best land" had many additional circumstantial benefits not assessed in its price, like proximity to water sources, easy access, easy to trade etc. and more.

An additional example would be paying a $1000 debt with $100 or $1 bills (as the Gemmorah claims that the debt could be returned with crops). Even if that's the same monetary value, one is perceivably valued more.

So paying with the best land does not pay the exact amount of debt, but losing additional benefits not included in the price.

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It should be noted that nowadays we tend to assess the value taking into considerations all possible pros and cons. it reminds me that some 20 years ago, here in Israel, the semi-official price list for a car only included the model and the year. Today it has more than 10 additional features, like types of previous ownership, mileage and more.