In principle, I see no conflict between homelessness or vagabonding and Capitalism. What we have today is "homeless" and "vagabonding" capital, products, services as well as companies and jobs (or at best migrating). These are more of a problem than a person not having a fixed home, because to cope with globalization one has to become homeless and vagabonding as capital, products, companies, and jobs are, IMO. Home ownership or even rental accommodation carries with it a load of bureaucracy/red tape and various tax related burdens that the libertarian thing to do is not to have a fixed home.
After all, the "market", the real "market" was always in the streets with street vendors and open bazaars. That is where it all started and then bureaucracy etc etc "took over".