“but the transferor, or their heirs, can go to court to get title back. If they demonstrate the restriction has been violated and the judge agrees, they win.”
Only if the judge is a member of the 10th century Church of England.
Imagine a piece of property owned by 10 people over a century. Each owner adds a deed restriction to that property. The “dead hand” of 10 different owners reaches out and demands that each restriction be honored by the present owner. Then it’s no longer private property.
What if one deed restriction conflicts with another deed restriction? Which restriction takes precedence?
Common law does not recognize “dead hand” deed restrictions.
You can google case history if you like. If the deed is written correctly it can be enforced. Has to have precise wording, and in the case of heirs, it has to be a “closed set” of people, as opposed to open. E.g., you can’t say “all future decendants” but you can say “grandchildren alive at the time of my death”, or what not.
Also can vary by state. Perpetuities have always been unenforceable, however, if I recollect correctly, Florida has a 360 year limit.