The following is background text to Lk 16.1–9. The Roman author Columella (AD 4 to ca. AD 70) has an extensive passage on the ideal calculations landowners should make in land property management, especially regarding the type of labor they should use (direct management with slaves, vs tenants under fixed contracts, vs sharecroppers?):

After all these arrangements have been acquired or contrived, especial care is demanded of the master not only in other matters, but most of all in the matter of the persons in his service; and these are either tenant-farmers or slaves, whether unfettered or in chains. He should be civil in dealing with his tenants, should show himself affable, and should be more exacting in the matter of work than of payments, as this gives less offence yet is, generally speaking, more profitable. For when land is carefully tilled it usually brings a profit, and never a loss, except when it is assailed by unusually severe weather or by robbers; and for that reason the tenant does not venture to ask for reduction of his rent. But the master should not be insistent on his rights in every particular to which he has bound his tenant, such as the exact day for payment, or the matter of demanding firewood and other trifling services in addition, attention to which causes country-folk more trouble than expense; in fact, we should not lay claim to all that the law allows, for the ancients regarded the extreme of the law as the extreme of oppression. On the other hand, we must not neglect our claims altogether; for, as Alfius the usurer is reported to have said, and with entire truth, “Good debts become bad ones if they are not called”. [….]

But when the climate is moderately healthful and the soil moderately good, a man’s personal supervision never fails to yield a larger return from his land than does that of a tenant — never than that of even an overseer, unless the greatest carelessness or greed on the part of the slave stands in the way. There is no doubt that both these offences are either committed or fostered through the fault of the master, inasmuch as he has the authority to prevent such a person from being placed in charge of his affairs, or to see to it that he is removed if so placed.

On far distant estates, however, which it is not easy for the owner to visit, it is better for every kind of land to be under free farmers than under slave overseers, but this is particularly true of grain land. To such land a tenant farmer can do no great harm, as he can to plantations of vines and trees, while slaves do it tremendous damage: they let out oxen for hire, and keep them and other animals poorly fed; they do not plough the ground carefully, and they charge up the sowing of far more seed than they have actually sown; what they have committed to the earth they do not so foster that it will make the proper growth; and when they have brought it to the threshing-floor, every day during the threshing they lessen the amount either by trickery or by carelessness.

For they themselves steal it and do not guard it against the thieving of others, and even when it is stored away they do not enter it honestly in their accounts. The result is that both manager and hands are offenders, and that the land pretty often gets a bad name. Therefore my opinion is that an estate of this sort should be leased if, as I have said, it cannot have the presence of the owner.