I have always loved the idea of living on a sailboat. Its a long way to the hospital if/when you need it and security is a real problem. The reality is that plan is only avoiding the real problem by attempting to fly under the radar. imo, that is a temporary fix that will also disappear.
Whatever the 'solution' there are always obstacles. I think that space is a lesser obstacle than politicians and bankers and dealing with them involves use of force... at present that would be suicidal, even higher risk than space travel. Eventually, either there will be war for liberty or those who want it will require a new frontier. That frontier will have to be out of reach of the statists.