It is my understanding that the Dhammapada was written at least one hundred years after the Buddha's death. Also, these words are not the Buddha's but are of his disciples who may or may not have been enlightened and one might speculate that those who actually wrote down these words most certainly were not enlightened. In this way the Dhammapada is much like the Christian New Testament which also refers to third-hand interpretations of a liberated being. As such, I find some of the translations quite wanting.
Some of this is undoubtedly "lost in translation" effect which is why reading ancient philosophical ideas as religious text is so dangerous. Jesus said, "seek and ye shall find" and the Buddha said something like, "don't take my word for it, figure it out for yourself."

Verse 85: A Few Reach the Other Shore
This is certainly true, but it condescends to those who try but don't achieve liberation as if being an Arhant is the ultimate class distinction, which fits nicely with the cast system of India. It also explains why Buddhism took off in India early on but is falling from favor as a religion in modern times and being replaced by Islam and Christianity, religious illusions more easily grasped by the majority who will never understand actual liberation.

Verse 63: Know Reality, Be Wise

Yes, the person who believes he is wise by virtue of mundane knowledge is the fool, and the person who realizes mundane knowledge is illusion is wise. "Know reality" simply means do not confuse what goes on in your head with reality. Only consistent watching of the mind can reveal that. Reality is what is, not what you think it is.

Verse 64: The Ignorant Cannot Benefit From the Wise.
This statement is also condescending, both to the wise and the the ignorant. Makes a wise person think, why bother to impart wisdom?

You can lead a horse to water but you cannot make him drink. Wisdom is always a positive thing. Some will get it, others will not. People are like fruit hanging on a tree. Some will ripen and fall of their own accord, while others will remain green their entire lives.

Verse 70: The Unconditioned is the Highest Achievement
This is certainly true, but why does it devolve into a value judgement placing the liberated person at the top of a hierarchy with the seeker wallowing in his delusion. Ascetics also achieve liberation as do those who merely stumble upon realization like Peace Pilgrim and Ekhart Tolle. The Buddhist path is not the only one and this condescending translation/analysis is the very crux of religious exceptionalism, which is the absolute opposite of what the Buddha taught.

Verse 72: The Knowledge of the Wicked Splits His Head.
The verse is true while the explanation is vague. The more mundane knowledge you learn and believe, the further from liberation you get. I'm not sure who the "wicked" are, but the one who seeks power tends to accumulate knowledge of the material world in order to elevate his own status at the expense of others, splitting his head with the insanity of separation. The forest monk harms no one and the one who achieves Buddhahood is a light unto the world.

Verse 43: The Well Trained Mind Excels People.
This is a convoluted and easily misunderstood passage, lending the idea that filling the head with "knowledge" is to become exceptional. I interpret it as, other people don't have the answers you seek, you must discover them for yourself. If you only believe what other people tell you, you will go nowhere spiritually and you must discipline your mind to unravel the illusions it encounters moment to moment.

This was fun. You are obviously a brilliant person who loves to think and I enjoy your posts immensely. Thanks for the provocation.