I'm teaching first-year Property this semester for the first time in five or six years. We just completed the chapter and estates in land, and are about the start the chapter on future interests. Prepping those two chapters for class has reminded me of what so many non-lawyers detest about lawyers and the legal system: seemingly unbreakable commitments to antiquated rules that make no sense today, and probably made no sense when they were first adopted.
First, the complexity of the rules is such that no one who is not carefully trained in the law could confidently engage in estate planning or lifetime conveyancing of any but the simplest interests without hiring an attorney. If they do not have a lawyer, they risk having their intent ignored or mangled by judges who draw irrational but consequential legal inferences about intent based on the use of innocent-seeming phrases, like "so long as" and "but if."
For example, if a husband dies leaving land to his wife "for so long as she remains unmarried," that is considered a valid conveyance of a defeasible life estate based on the husband's imputed intent to take care of his wife until she remarries. However, if the husband used slightly different language, "to my wife, but if she remarries..." the courts would construe that the husband intended to restrain his widow from remarrying, which is against public policy (except for non-heterosexuals in most states).
The inanity of these differential judicial inferences is compounded by the ease with which a well-advised spouse can combine the offending intent of restraining his wife from remarrying with the correct language to have that restraint upheld. Meanwhile, the condition itself (remarriage) creates an incentive for the surviving spouse to shack-up (that is, live in sin) rather than remarry, an incentive which courts do not factor into their public policy considerations.
And don't even get me started on the scholasticism of the Rule Against Perpetuities (RAP), which I haven't taught in nearly 15 years because it has been increasingly trivialized (where it has not been nullified completely) by changes in tax codes and other legal rules facilitating the rise of monied dynasties, which the RAP initially was created to prevent. Legal changes abolishing or marginalizing the RAP have increased the power of the dead to control land forever (more or less), and have contributed significantly to the "new gilded age" in America, where social mobility, up or down, has become more difficult.
Unfortunately, my colleagues convinced me to teach the RAP this semester for the sake of (a foolish?) consistency in our Property curricula. So next week, against my own better judgment and against the tide of history, I will be teaching about ridiculous juridical presumptions concerning "fertile octagenarians" and "unborn widows."
Jeremy Bentham famously referred to presumptions of natural law as "nonsense upon stilts." I think that phrase could just as well apply to some of many of common-law rules governing estates in land.