Introducing interoperability among spatial datasets and registers is one of the key drivers for optimizing public administration, starting from the simple automation of existing processes, to the overall transformation of the system, and the construction of modern user-oriented services. An additional incentive for such a transformation, in the European context, was the foreseeable need for interoperability between the national systems of registers and the European Union (EU) registers, and potentially in the future with other registers worldwide. A key prerequisite for the realization of interoperability is digitalization. Digitalization is the most important step towards the development of an effective 3D Land administration. LADM country profiles integrate the legal and institutional context governing Rights, Restrictions and Responsibilities (RRRs) with the desired Land Administration Systems’ (LASs) advancements. A significant number of countries have developed LADM-based country profiles. Experiences from these developments are in the direction of integrated Land Administration, which the LADM data standard provides, with a vision for the future and can serve as good practice for the countries. This paper compares the digital transformation of the land administration in two vastly different case studies, in one EU country (Croatia) and in one Caribbean country (Trinidad and Tobago). A Comparison of these two land administration systems and their different tracks toward the development of a 3D land administration system that would address their differing social and economic needs within their individual resource and skill capacities was investigated in this paper. It was found, after comparison, that the step by step process to further and develop from the existing status to a 3D cadastre that is LADM compliant is differentiated according to the needs, capacities, and resources available in each of the countries. Countries would do well to decide on their individual social and economic needs and capacities prior to embarking on a step by step process toward 3D land administration.