The dawn of the era of the Internet of Things (hereinafter, IoT) is the perfect time to improve the quality of legal regulation. On the one hand, the development of such regulatory framework is at the start, on the other as a new "version" of the Internet, it inherits, but reconsiders issues of principles and pervasive problems. Regulation of the Internet of Things (hereinafter, IoT) should evolve, at a minimum, in due regard to the principles of user awareness and freedom of participation in the Internet of Things ecosystem. That being said, further development in this respect would flow through the following "pain points" which can be considered as pervasive problems of the Internet of Things: information as commodity, personal data and privacy, net neutrality, cybersecurity, compatibility and competition, artificial intelligence (hereinafter, AI) and smart contracts, decentralized networks. In this paper, the IoT is considered as a phenomenon that, overall, is expanding the information space to the world of physical objects, serving as a "bridge" between the different stages of human progress in information society. The IoT is creating new and fundamentally-complex "rules of the game" for the legal system. Technological progress always outpaces the law, yet the law remains one of the most important instruments for the organization of social and economic life, and reasonable compromises are essential. In the future "IoT world" the legal system must provide the basic prerequisites for self-regulation and dispute resolution. In this regard, while assessing the approaches to regulating the IoT relationships, the authors connect the practical pervasive problems to a broader theoretic context of semantic limits of law in relation to the technological development. The paper suggests dividing the technologies into those of immediate impact that already have convertible social, economic or political value (an approach broadly inspired by T. Parsons), and those that only strive for it, on a case-to-case basis. The former allow reasonable development of law now, while the latter may reasonably allow that in midor long-term perspective which could allow flexibility between regulation and incentives for development.