What's considered bold today was common place 70 or more years ago!
No Gyro approaches (they are still available today)
NDB approaches with a fixed card and/or a manually turned antenna.
Low Frequency Radio Range approaches in bad weather at night
Dead Reckoning let downs in the Himalayas flying the Hump
Go back to WWI and you see flying up through clouds with virtually no instruments (using the compass and airspeed only), flying in weather where the ceiling was less than 100' and 400 yards and fighting your adversary, cruising at 20,000' for 2 hours with no oxygen in an open cockpit biplane.
Flying Lighted Airways at night in the snow delivering the mail.
Going across the country on Colored Airways (who knows what Colored Airways are?)
Today we call these things crazy.
I might even consider circling approaches at night a bold maneuver today!