Yes He does understand and He cares. This is why He asks us to cast all of our cares on Him because He cares for us. Jesus was a Man of sorrows and of tears, so His heart is touched with our griefs_ when the days are weary and the long nights dreary, O, yes, I know my Savior cares.
I believe Jesus entered into the entire spectrum of human suffering and experienced it to its fullest expression. In other words, in terms of suffering, if it can be experienced, He experienced it. Not only did He experience it, but He endured it, beat it, and will one day banish it for eternity—all for me and you! “For we have not an high priest which cannot be touched with the feeling of our infirmities; but was in all points tempted like as we are, yet...