The shitty part of USB-A is that the tactile feedback of being slightly misaligned is identical to it being upside down. My experience tells me no amount of vigorous jiggling or extreme self-confidence will ever allow for consistent average 1.5 attempt plugins.
All the standards before USB were in my memory even less user-friendly — trying in vain to reach behind a heavy computer and unscrew the two jammed retaining bolts holding in a serial, parallel, scsi, vga, or DVI plug with slippery bent plastic jacketed heads. Almost zero clearance from the plug case, that really did suck. Screw it in slightly loser next time, now you’ve got a flickering monitor, dummy.
And ps2/mini-din connectors sucked too - having the connector off-center or at the wrong rotation also felt quite indistinguishable.