The basic law relating to online terms and conditions has been stable for some years now and should remain so. It certainly is not headed for a "reckoning."
When private parties transact business in a free society, the law of contracts steps in to provide rules enabling them to do so in a well-defined and orderly manner. Contract law has some fundamental principles that anchor it and, beyond those, has a vast number of intricacies that potentially can come into play in individual circumstances. Concerning fundamentals, for most executory contracts to be enforceable, you need to have mutual consent and some exchange of consideration. That is, a meeting of the minds on material terms and an exchange of value. When these elements exist, the law considers a contract to be binding and imposes legal consequences for any breach or failure to perform. In order to avoid chaos, it further stipulates that the core principle (meeting of the minds) is not based on purely subjective factors but on what a reasonable person would believe in the circumstances. This objective standard enables commercial transactions to proceed without endless second-guessing about what the parties might have desired or meant when they contracted in any given transaction. Because of this, while it can easily become messy in any given case, most contract situations can be legally evaluated with a fair degree of certainty and parties can plan their affairs and determine their rights accordingly.
The above describes what might be called a very high-level summary the central tenets of the common law of contracts in the Anglo-Saxon legal tradition. If someone reasonably can be said to have consented to a given transaction involving some exchange of value, legal rules applied to govern how that exchange took place and what would happen if some breached his or her agreement.
When it comes to terms and conditions in online commerce, the law generally applies this body of contract law but does so via what might be called the fiction of mutual consent between the contracting parties. It is well known that the vast majority of persons do not bother to read such terms and conditions when they click on the "Agree" button. Nonetheless, the terms and conditions are legally binding upon such persons. Why? Because it is assumed that the person read and understood them in clicking. And that assumption is what makes it a fiction. In effect, the law says, "we will pretend that the person read through the terms and knowingly agreed to them." Given that this legal fiction effectively substitutes for a true consent, the law can proceed along its merry way and treat this contract as it would any other, i.e., treat it as binding and enforceable upon the "contracting" party. In effect, to preserve orderly rules of contract in such transactions, the law effectively says that the terms and conditions are legally binding if they are such that a reasonable person who had taken the time to read through them would have understood them to have a certain meaning (that is, the "reasonable person" meaning that the law will enforce upon the person doing the clicking).
This fundamental approach to terms and conditions in online transactions has not changed one bit in some years and is under no risk of being changed. Because, without it, you could not practically have any semblance of legal orderliness in online transactions.
Moreover, while it is often said that dense legalese is undesirable in such situations, courts generally enforce such legalese without hesitation, even if a complaining consumer says until he is blue in the face that it could have been put in easier-to-understand plain English. There is no legal rule that requires contractual language to be put into plain English and there are some types of contracts where an attempt to express the legal requirements in that way would cause a loss of precision or lead to other problems. Whether something is expressed in plain English or not, then, typically does not affect its enforceability in online transactions.
Again, nothing pervasive is happening in the law affecting online transactions so as to require use of plain English to make terms and conditions enforceable.
None of this is to say that there are no protections in existing law when people try to use weasel language to defraud others or use language that is so imprecise as to mislead consumers or use language that is so ill-defined or vague as to leave important matters uncertain to the other contracting party. In all such cases, existing common law has remedies of varying kinds to say that such contracts are unenforceable or that some remedy applies in favor or an aggrieved or defrauded consumer. But, in practice, these are edge cases, the ones that wind up in dispute or in court. The vast bulk (99%+) of the commerce that occurs is covered by the general contract rules and proceeds in an orderly way because the rules are known and predictable.
Against this background of the common law contract rules, it is possible for persons to want to modify the existing rules on grounds that such rules are unfair to the consumer and or are not based on true consent by that consumer or for some other public policy ground.
This is where special public-policy-driven enactments come in to modify the standard contract rules. Legislatures can adopt special laws dictating outer bounds to how businesses can use the private data of consumers as such data may entrusted to them. In this area, perhaps, a form of "reckoning" may occur if it is determined that companies such as Facebook ought not to be able to sell or misuse private data to the detriment of their users. This is an important development and serious changes may be afoot affecting such special areas. But this does not affect the general principles by which online contracting occurs.
There could also be proposals mandating that plain English be used in terms and conditions or requiring this or that form of mandated disclosure to help ensure greater consumer understanding but all such proposals come with decided trade-offs that typically make them impractical. The reason for the fiction of legal consent in the current system is the supreme utility that comes from allowing millions of online transactions to occur every day without incident based on orderly rules known to all. You can change all that through legislative enactments saying that public policy requires a different system that is more fair to consumers. But at what price? That is why the current system is and remains solidly in place.
To underscore the importance of utility, I have been legally trained and have years of experience such that I could easily read through and comprehend the legalese that is found in most online terms and conditions. Yet, with rare exceptions, I am just like everybody else and will click "Accept" or "Agree" without reading anything and without a second thought. As a lawyer, I can't say that I am proud of this but I can say this is human nature. The issue is not primarily that legalese or plain English will make a difference in understandability. It is that we take the path of least resistance when not much is at stake and we don't want to be bothered. Try as we might, no law will solve that problem.