How do I / Should I, console a former classmate and stressed out PHD/MD applicant? I have a former classmate of mine who wasn't successful in his/her application to top-tier PhD/MD programs this past application cycle. 

Over the phone and through email, I've been sympathetic when I learned about his/her disappointment and offered words of encouragement, reminding him/her of their worth ethic (working 2-3 jobs at the same time and maintaining a stellar GPA) and personal aspirations (the kind of aspiration where you think that he/she would be a major force in research, selflessly serving the needs of others, and accomplishing a great deal in their career) during our undergraduate years.

However in recent time, I've lost touch with this person for unknown reasons, as I stopped hearing back from them. Distance, time, busy with other stuff. I don't know.

The question I wanted to pose is, should I try to reach out again? 

If they decided to reapply, what little would my words of encouragement offer beyond a smile and good wishes? (I doubt they would have an impact on the actual admissions board)

If they decided to not reapply, wouldn't my words just pour salt into an otherwise fresh bitter wound in their mind?

Mind you, I am going through the testing phase at the moment myself and am narrowing down my PhD study programs to a handful for application, so I can't claim that I am in similar waters.

Put yourself in this person's shoes, how would you react in either scenario?
If you decide to reach out again, I would try to reconnect over a different topic first. It sounds like it has been a while since the results were announced, and bringing up their past disappointment over and over again will probably not help them get over it. If all of your interactions are focused on this one topic they might start to wonder if you are either secretly judging them about it, or if you are just pumping them for advice on what mistakes to avoid in your own applications.

If subsequently they bring up the topic on their own, you can express sympathy at that point. But I would follow their lead in whether they want to dwell on it or not.