Nice post. I totally see your point about how even if someone is struggling with something I think is silly, to them it might be more pain than I could imagine.
On the other hand, I'll share something a meditation teacher once said:
"An awakened person sees the suffering of others as a parent sees a child who has just had a nightmare. The parent feels for the child, they know what they are going through is scary and they want them to feel better, but in the end, they know that what they fear is not real."
That quote is spot on! I totally agree, it's almost like we have to let individuals navigate through their own turmoil to figure themselves out. When we try to look like we know the answers to everything and tell someone how to feel about something, their instant reaction is to go against the advice you've just given them.