[...]
I think that in fact the
Entwives had disappeared for good, being destroyed with their gardens in the
War of the Last Alliance (
Second Age 3429 - 3441)when
Sauron pursued a scorched earth and policy and burned their land against the advance of the Allies down the
Anduin (vol. II p. 79 refers to it). They survived only in the 'agriculture' transmitted to
Men (and
Hobbits). Some, of course, may have fled east, or even have become enslaved: tyrants even in such
tales must have an economic and agricultural background to their soldiers and metal-workers. If any survived so, they would indeed be far enstranged from the
Ents, and any rapprochment would be difficult - unless experience of industrialized and militarized agricultire had made them had made them a little more anarchic. I hope so. I don't know.