Concerning the fate of the entwives:
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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 policy and burned their land against the advance of the Allies down the Anduin (vol. II p. 79 refers to it2). 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 estranged from the Ents, and any rapprochement would be difficult – unless experience of industrialized and militarized agriculture had made them a little more anarchic. I hope so. I don't know.
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That is Tolkien in Letter 144, it is a long and interesting letter for anyone that hasn't read it yet.
Also, the Old Forest and Fangorn are the last remaining pieces of the ancient forest that used to cover all of the land between the two. It would be only natural for the trees in the Old Forest to be similar to those in Fangorn, so hourns they may have been. Also it is stated that trees become more and less entish over the years, waking up and going to sleep all the time.
One reason Old Man Willow could be seen as a huorn could be because he was aggressive and tried to kill the hobbits, adding to his agressive nature would be all the past transgressions against him. The wars from the nearby Downs and the hedge war with the Shire would have made Old Man Willow a grumpy gus.
There is other material out there concerning the Old Forest, if you want to know more, I suggest taking a look.