One of the main objectives of a perpetual traveler should be positioning. The logic is simple, with the rise of supranational organisations like the EU and Mercosur, it has become possible to acquire the right of abode for entire continents, often quite easily. For example, by becoming a French citizen one acquires the right to live and work in nearly every European countries. Similarly, someone acquiring the citizenship of Peru can expect to benefit from freedom of movement and equal opportunities in nearly all of South America as soon as Mercosur finalizes implementation (half-restricted freedom of movement is already possible).
This freedom of movement also opens the door to a number of interesting shortcuts. For example, it takes only two years to qualify for naturalization in Argentina instead of the 3-5 required in many other Mercosur countries. As such, someone could immigrate to Argentina with the intention of relocating to another Mercosur member-state once citizenship has been acquired. The same thing is also true in the European Union where several shortcuts exist and the CARICOM where some countries sell their passports.
As of today, four supranational organizations grant some form of freedom of movement to their citizens. The European Union is by far the best known, the other three are USMCA, CARICOM and Mercosur.
The benefits of having access to so many countries through those organizations are fairly obvious, imagine having the right to live and work in dozens of countries!
While most opt to go for only one new citizenship, it may interest some to know that it is currently possible to acquire citizenship in each of the organizations listed above in only a little over five years total (in the right circumstances).
Now onto the more technical stuff. The EU offers full freedom of movement to all its citizens and even to its permanent residents (certain conditions applies). On the other hand, CARICOM and USMCA offer freedom of movement only to qualified professionals. Qualifying as a professional in a CARICOM member state is very easy and should not be a problem for most nomads. In USMCA countries, however, only certain professions are eligible. They are: Accountant, Agriculturist, Animal Scientist, Apiculturist, Architect, Astronomer, Biochemist, Biologist, Chemist, Computer Systems Analyst, Dairy Scientist, Dentist, Dietitian, Economist, Engineer, Entomologist, Epidemiologist, Forester, Geneticist, Geologist, Geochemist, Geophysicist, Graphic Designer, Horticulturist, Hotel Manager, Industrial Designer, Interior Designer, Land Surveyor, Landscape Architect, Lawyer, Librarian, Management Consultant, Mathematician, Meteorologist, Nutritionist, Occupational Therapist, Pharmacist, Pharmacologist, Physician, Physicist, Physical Therapist, Plant Breeder, Poultry Scientist, Psychologist, Recreational Therapist, Registered Nurse, Research Assistant, Scientific Technician, Social Worker, Soil Scientist, Silviculturist, Teacher, Technical Publications Writer, Urban Planner, Veterinarian, Vocational Counselor, Zoologist. For US / Canadian citizens, no visa needs to be pre-arranged as resident status can be claimed directly at the border. For Mexican citizens, however, a visa has to be pre-arranged. USMCA resident status (known as TN status in the US) is valid for three years and can be renewed indefinitely. As for Mercosur, unrestricted freedom of movement has not been implemented yet. It has been approved and a timeline has been set but given how slowly Latin American bureaucracy tends to move I would say that implementation even by 2030 is unlikely. Currently, Mercosur citizens are granted a two-year work visa when moving to other member states and benefit from an easier pathway to permanent residency. Baring some major disaster, implementation will happen and considering the growth potential of the continent, I recommend including a Mercosur citizenship in your plan.
Adding depth
When planning a positioning strategy, it is also important to consider the far future. Circumstances change and a great option today may become a poor one tomorrow.
Population
The rate of population growth will affect everything in a country from quality of life to real estate prices to government policy and most importantly, to the economy. For example, a fast-growing population will present one with fantastic economic opportunities but several challenges in the form of resource stress, pollution and increased competition for school places, jobs, hospital beds etc. Fast-growing countries also tend to contract faster, once they have reached the top of the population pyramid, than slower growing countries.
Culture
Culture is another factor that you definitely cannot afford to ignore. It influences the way people behave and countries are run by people. Look for things like the national attitude towards work, politics, unions, debt, money, health, the environment, travel, corruption, education and leisure.
Economy
Considering the long-term economic prospects of a country is an obvious one. Look for things like debt levels, GDP growth over the last few decades, wealth equality, average salaries, taxation, average net-worth, house prices vs income, growth in retail and commercial space, the number of startups per capita, the number of businesses per capita, the number of patents per capita, reserves of natural resources, agricultural production, infrastructure, investments in infrastructures and English proficiency just to name a few.
Education
The way a country educates its people can greatly affect its future prospects. For example, a system of education which focuses mainly on memorization and discipline will produce a very different type of workforce than a system which focuses more on practicality and creativity. The Education index can provide some interesting insights but for a clearer picture I recommend joining local student groups and visiting universities in person (especially if you have / plan to have kids and wish for them to attend university).
Medical care
The quality of medical care is an important factor as it shows how efficient a government is at running a large, mission critical program. This is true even in countries like the United States where most of the medical infrastructure is privately-owned. You can read this OECD report for some insights into the future of healthcare in the developed world.
Crime
A high crime rate can be a deal breaker for many, for good reasons. Current violent crime rates are not necessarily indicative of future crime rates, however, and one can look at historical trends, social cohesion, gun prevalence, incarceration rates, rehabilitation methods and government policy to gain a better understanding of where things may go. The legalization of psychoactive substances and prostitution can also have a major impact on future crime rate (usually a positive one).