We landed on the Moon in 1969. It is a crying disgrace that we do not have a functional Moon base today, and I fear I won’t see it in my lifetime.
I’m also afraid that we won’t see public repudiation of religion, nor will we see a President / Congress elected with the balls to massively slash the Federal Government down to half its current size.
The Republic of Canada.
Seeing as how every time the economy is in the toilet the government raises the damn retirement age at least once, at this point I fear I’ll never see the day when Canadians born in 1992 retire. Not everyone lives to be 80!
Sure, but wouldn’t it be nice to be screwed over by a democratic republic than a constitutional monarchy! 
Universal healthcare in the US.
I fear I will not see the second Obama term.