I attack your central point thusly; with a verbose aimless harangue composed under the veil of a hangover:
You imply that considering the possibility of being born in the wrong time period is somehow deep or meaningful. And also that this is a problem that should not be ignored or else risk serious consequences.
It is not meaningful because it's a line of thought that leads to no useful solutions for everyday life.
As time travel more than likely does not exist or ever will exist, you will never end up in some romanticized era.
The closest you can get is immersing yourself in role playing or when computing becomes advanced enough to handle a convincing virtual world that's not populated with giant talking penises, dive right in. But this is just escapism and fantasy.
It's possible that virtual reality program actually already exists, and that you're in the matrix right now... If so, what are you going to do about it? Nothing, that's what.
Well, maybe a god or goddess plucked your embryonic self out of a dark-age uterus and switched it with your mother's true child. If so, what are you going to do about it? Nothing, that's what.
Of course, if you feel you should have been born in the stone age, there are still places on earth where people live like that. So go join them!
In the same vein of thought that >>12 mentioned, there are new-agers that believe in reincarnation. It seems a large number of these people were Cleopatra in a previous life. Bullshit, obviously they can't all have been Cleopatra. All sorts of people, from dead stupid to brilliantly intelligent, look at these people as narcissistic loons. As they should, the same way you'd look at one of the many people living right now that believe they are the second coming of Jesus.
Of course I don't say considering 'the deep meaning of life or issues connected with existence is shallow or stupid'. That's you putting words in my mouth.
The closest thing to meaningful questions posed by >>1 would be: Has modern technology and social development left us feeling disconnected with the natural world around us, and so each other? Is there some animal need in us to walk naked through the brush, sleep under the stars, and shit in the woods? If so, how can we satisfy this base instinct if we don't take measures to ensure conservation of woodlands, wetlands, rain forests, etc? How can we compassionately maintain an equilibrium of the human population while remaining human ourselves? How long do we have before the size of the human population is no longer sustainable? Can we consider Mars as a possible lifeboat for spaceship Earth?
But none of these are 'Personal Issues'.