Great article! I like the flexibility of SafetyWing with respect to home country treatment. However, I have been reading up on the terms and conditions, and found the following issues:
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Repatriation (e.g. getting flown back to your home country for treatment in case of serious illness) is not covered, unless you are dead or your visit is to the US. This is one of the main reasons for choosing a travel insurance as an EU citizen travelling withing the EU. But of course, as a nomad, you may no longer be eligible for social security in your home country anyway, so it is individual whether this is a concern. Bedside visit (having a relative getting flown in to visit you in case of serious illness) is, however, covered.
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Pepole involved in vivid sports (and also some normal ones) should check the list of sports excluded from cover thoroughly. For example, American football, soccer, and kite surfing are not covered. So don’t play soccer in your coverage period (which may be full time if you pay every month as a nomad)…! And stay away from the kite surfing school on your vacation / life as a nomad.
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Unclear wither Search & Rescue costs are covered. For instance, if you have an accident breaking a leg while doing recreational downhill skiing, you will get a large search & rescue bill if you are not covered by your insurance. But maybe you have an accident insurance which covers this.
Personally, for shorter travels, I prefer Bupa Global, which covers these things (exept for search and rescue I think) by default and also allows for trips to start/end outside of your home country (but no treatment in the home country). It is correspondingly more expensive. But of course, this is always individual, and people should in general read the terms and conditions carefully, as you note.