Are there any examples in canon that show Dumbledore attending to the welfare of a Hogwarts student in as caring a way as he looked after Harry and, covertly, Draco Malfoy?
I almost want to include Tom Riddle Jr on the list above, as well, but Dumbledore didn't keep an eye on Tom Riddle out of altruism. Dumbledore was suspicious of Tom Riddle's psychopathy, and kept a close watch on Riddle accordingly.
Are there any other students¹ Dumbledore reached out to, or did he leave that to the Heads of Houses? If indeed he did show concern and caring towards another student, how did he demonstrate this?
★ I do not prefer an answer from the HP Wikia or the Wikipedia.
¹Students from any era during which Dumbledore was Headmaster of Hogwarts are eligible for any answer to this question.
Answer
Yes.
One example was Neville. Dumbledore both told Harry about Neville's past so someone could have a basis of treating him better than a squibby loser (and Harry was a perfect person to tell as he could share Neville's pain). BUT he also asked Harry not to spread that story around, since that could do damage to Neville as well.
Another example was his covering for Ginny Weasley to make sure the Chamber of Secrets was explicitly blamed on Riddle and not her.
Another one was obviously Hagrid, whom he convinced prior headmaster to hire after expulsion from school (thanks @b_jonas for clarification)
But remember that he only cared about Big Things. He only cared about Malfoy as far as not making Malfoy into a murderer with broken soul.
And he didn't really show all that much care about Harry's emotional well-being, for a good reason: Harry had to be tempered and trained for his destiny, not coddled.
Remember, his job was running the school AND destroying Voldemort, not showing random acts of caring towards the students. An hour spent seeing to comfort of Dean Thomas was an hour NOT spent hunting down Horcruxes.
A very good fictional equivalent would be Colonel Graff from Ender's Game. He deeply cared about Ender. Which didn't stop him from acting in the worst way possible as a human being to get Ender to save the Human Race.
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