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A guarantor of the Ketubah obligation is not obligated to pay - he is just encouraging the couple to marry.
A creditor collecting from the deceased father's estate is entitled to the
worst land only. If orphans are minors, they are protected by not having to deal with selling the worst land. If adults, they do not know the affairs of their father, so an oath that the debt was not paid is required.
Creditors collecting from the estate first collect from available property, and only then proceed to repossess from purchasers those fields on which there is a prior lien.
We explore the status of orphans in antiquity.