Most difficult imho would be to explain why we haven't advanced any further. If the person is 50 in 1950 he started with horse carriages and saw development to intercontinental bombers, rockets etc. The landing on moon would astonish him, advances in medical sciences and computing too but he probably would ask: "And what are you using that neat little gadgets for?"

Liftoff does the trick for me

the archerall!

Good old Sid Meier's Civilization - Beyond Earth. I really love this game for it's slow pace and depth.

Syndicate and Wing Commander Privateer

Maybe I'm underestimating individual benefits of digitalisation. But I tried to remember talks with my grandfather. He was born in 1912 and lived to the age of 87. He could remember the coronation of the last austrian-hungarian emperor Karl. People then were not as individualistic as we are today. Technological, social or cultural advancements were seen more on a collective scale. The mere possibility of calling or texting someone didn't impress or astonish him much. Especially in the 50's and 60's promises of a bright and shiny future were made. Just think of the exploration of space or the deep sea with proposed bases on moon, mars or the seabed. It wasn't called the atomic age for nothing. What I experienced was that those now long dead relatives appreciated the individual improvements of their lives but they felt a certain slow down in regard to an overall progress of society.

I'm using metager and I'm quite satisfied with it. https://metager.org/

It's a meta search engine run by a nonprofit. If you want to know more: https://metager.org/about