I have found San Diego and surrounds to be very nice. Unfortunately, boondocking in some of those areas might be challenging. I certainly would be happy to wander there, but winter is long and constant moving in urban settings might be unpleasantly stressful over time. Stress is the antithesis of the purpose of the hobo lifestyle, so I have virtually explored alternatives.
Palm Springs has appealing weather statistics, but from what I have seen online is not an environment particularly accepting of boondocking. There are some pleasant camping options nearby, however, and certainly Palm Springs is high on my list of wintering zones.
The Slabs, or Slab City, is south of Palm Springs, very near the Salton Sea. Again, worthy of a visit, but from what I have learned of Slab City I don't particularly want to dwell there. It is a rather lawless place, and I am growing too old to deal with that.
The Salton Sea caught my eye. I explored some options, and learned that a patch of land can be had there for less than ten thousand dollars. I suspect that camping on such a patch of land will have some restrictions, but those can be worked around. A place to rest, even if the accommodations are little more than a shed and a carport, electricity, and perhaps Internet access.
The shed could be even a bit of a tiny house. A storage place for some items, and even a small workshop. A cot and a nice chair. A place to dwell in moderate temperatures, from which journeys of days or weeks might be launched. The restrictions created by the current plague make clear that having a base camp is certainly a nice option. Other similar changes in the future might make having a base camp wise.
So, Imaginary Mike is in the market for a patch of land near the Salton Sea. Something simple, with little maintenance and a very low cost.