My fave era would have to be the 50's and 60's. Amazing things happening, sky's the limit, and the liability/entitlement culture hadn't set in yet. We could still have a few astronauts or pilots die each year pushing forward the boundaries of the possible, and it was tragic but certainly not something that would actually STOP us or get litigated to death. People who were willing to take great risks could do great things. We've lost that here in the US.
Per the '50s and '60s attitudes, spacex would have already sent a dozen or more astronauts up in their dragon capsule, which has yet to suffer a catastrophic loss of the capsule but which still isn't "certified" for human flight. 50-60 years ago, we'd be like "with all that money being spent you STILL haven't sent up a human in that thing?" We built the Apollo program step by step, the SR-71, X-15, computer chips and a TON of new medical technology, Teflon, etc etc. Then we got so risk adverse that our idea of a really risky idea is starting uber taxi service in a city with unionized cab drivers, or coming up with a new service that uses the internet which was invented decades ago. Or putting a camera on a pair of glasses. Meh.
Give me the optimism and energy of the '50s and '60s please. I'd fly anything scaled composites builds, and ride along in anything spacex lofts into orbit. I'd do that tomorrow or as soon as the ink dried on the liability waiver. I'd do it for free. A whole lot of my heroes died in the first half of the last century doing great things, things that the nanny state simply doesn't let us do anymore even though it would be my neck I'm risking, not theirs.