But each time you say "You can do it!" what you're really saying is "I knew a guy who did 3 application cycles ago!"
I disagree... that's a really oversimplified and generalized presumption of what amounts to an extremely variably defined platitude. What you're doing is giving him a shot of positive thinking.
I am reminded of an anecdote when I first started getting into science and math after avoiding them for so long. When I found even the most basic of Trigonometry challenging, my friend would tell me to smile through it, and tell myself I could do it.
Through my undergraduate education I studied motivation and reinforcement as part of my Honors graduation thesis, and there is a nice body of evidence to support the fact that people, when encouraged rather than discouraged, tend to perform better than their control.
When I say, "you can do it", it is never without qualification. However, someone with a poor academic history (HISTORY) but with a strong "then vs. now" and a revised work ethic can certainly accomplish what you deem as impossible.
2.644 is a pretty awful position to be in, and in
this case, you are probably exactly right (Not withstanding Academic Forgiveness and the ability to set aside his past completely), but as a general rule, I don't know that I agree with your overall sentiment. If it was, say, 2.944 instead of 2.644, we might be having a different discussion.
I will be the first to admit that not everyone can get into everything. I will never be in the NBA or run a mile in 4 minutes flat, no matter how hard I try, there are certain factors set against me. And for many people, school (pharm, med, law, whatever) is the same... and this could be the same for OP.
Regardless, the information is good to have for the OP.