> I'm not a retard, how hard is it to break into this lifestyle starting from zero?
As hard as you make it,
Depending on your field of work it might be easy or completely impossible. Some Healthcare/Finance/Gov work can't be done out of state let alone out of the country. Tech is by far the easiest remote work that can be done, but it's dependent on many factors. You'll basically need to find what job field, most importantly you LIKE, and can do.
After getting into said field, you'll most likely need to pull 2-3 years MINIMUM at an office job proving your worth, as you have no experience you need to show you understand the gravity of projects and such. This is where most people get too cushy with a decent paying job or accumulate debt to step up their lifestyle and forget about the traveling since "well I can just do a fun 2 weeks in X" is more appealing. Once you have a resume built you can often forgo raises(in this economy) for WFH, most companies are using WFH as a "bonus" rather than give cash incentives. Once there assuming you can keep up with everything and work isn't cutting your balls off about working abroad; go enjoy it.
The biggest problem will and always will be getting through the first round of jobs to build the experience while keeping your eyes on the expat goal, while also being able to walk away from the job you built up at