Hi Adam, I can't want to get on the road myself! I was planning to do so in 2020 until COVID-19 hit and I figured I'd wait it out until things cleared up a bit. Well, it's 2021 and I'm still waiting.
I fear, though, the digital nomad opportunity is something accessible only to people from developed countries, and a much thinner sliver from the developing world.
I'm from a popular digital nomad destination - Malaysia - whose popularity, amongst others, is due to the relatively low living costs. The digital nomad lifestyle is simply not going to happen for most of my countrymen, for the simple reason there are limited places to go to lower one's cost of living if the place one is living in already has some of the lowest living costs in the world.
Although companies are going digital, few of those benefits will accrue to most Malaysians. For instance, a Malaysian company would pay a senior Java developer something like $30,000 a year. The average wage for a similar job in the US would probably be closer to $100,000 a year.
I doubt the Malaysian company would start paying their remote developers at US rates. One possibility, of course, is that a US company might start hiring Malaysian developers at US rates - but there would be the natural issue of cultural fit. And, I think US citizens would be rightfully unhappy if their companies were to start hiring foreign nationals in large numbers.
It'll be interesting to see what the shape of things to come will be like! I suspect new organisational structures will have to emerge once remote working scales up enough that the current solopreneur/remote consultant structure becomes unable to accommodate the crowd.