Understanding: person and/or issue?

A hungry homeless man approaches a well-dressed gentleman on the road and asks for alms or something to eat.  The gentleman with great concerns asks the other person why is he begging when he could earn something in a dignified manner.  The other person then narrates to him his sad state of affairs and unfortunate turn of events.  Given the pandemic and its domino effect, the gentleman does not need further proofs to understand the genuineness of this poor guy.  After listening to him and his sad state of affairs, the gentleman spends a few moments in silent reflection and then with great concern and passion lays bare the root causes of the plight of the poor man.  And after a really acute analysis of the situation, he assures the poor man that he will do something about the root causes and goes on his way.  Perhaps he does initiate procedures and policies that address the issue of hunger and homelessness. 

In another instance, the same hungry homeless man approaches a woman with the same request: alms or some food.  The woman listens to his story and then understanding the case to be genuine, buys him the same lunch that she ordered for herself.  She even recommends him to a particular location where homeless people are offered free shelter for a limited period.  And she goes on her way.  She does not really get into the long term issues of hunger and homelessness.  

The gentleman in the first instance understood the issue;  and sought to address it.  He did not feel the need to understand the person.  The lady in the second instance understood the person and did not bother about the underlying issue.  

Most of us would root for the lady rather than the gentleman.  That's typically a Christian virtue.  But even the gentleman's approach is also needed.  Our christian virtue somehow 'prevents us' from aiming big, addressing the basic issues.  (That's my take on the unfinished parable of the Good Samaritan).  

However, my interest here was the notion of understanding:  What matters most, understanding the person or the issue?  Why does understanding the person somehow feel 'better' than understanding the issue?  After all, there was constructive action in both instances.  If the lady used her heart to understand the poor guy, can we still call it understanding?  Is it not compassion?  Is not understanding related to the head, concepts, ideas, knowing?