I have to say, I agree with the traditional Christian practice that discourages this sort of monasticism, called gyrovagues[0] in the West. The more usual forms of monasticism, although they accept donations, are expected to me more or less self-sufficient on a daily basis, and thus less parasitic on society. Either a monk would live in a monastery and work to support the monastery, possibly selling some of the products to the outside world, or a monk would live on their own in the wilderness, only occasionally meeting with a priest and generally actively avoiding donors, at least for the first few years. An exception is anchorites, who generally spend all their time in prayer and do rely on donations, but they generally don't move around from place to place.

Even the large monasteries over time became less favored by the populace in Europe, since they had acquired enough land through donations over the centuries that they often began to act more like landlords.

In summary, those who wish to live outside of normal society, particularly economically, should strive to avoid being parasites, and, failing that, should not move from host to host.

[0] https://en.m.wikipedia.org/wiki/Gyrovague

The only difference is, at least in my experience, many hippies don't actually do the things necessary to create change. They are individuals touting a known consensus. It's the reason why green measures generally fail in politics but stupid things like protecting the second amendment are upheld strongly. There is no centralized institution to fight for these beliefs. This is why you see the Freedom From Religion Foundation actively fighting against many religious bills. It has a goal, the ability to garner funds, and a means to support people to achieve them. Most hippies are just getting by and eventually wake up realizing they need a job to survive once the donations wear out because they don't have a stable supply of people believing in their individual cause.

It couldn't possibly be that the inertia of the system at large is highly resistant to progressive policy?

"The system" is just the full stack of human avarice. The eradication of which had proven to be nontrivial throughout recorded history. As soon as someone wants more than the next guy, you have a system.