Another trick is that the USB standard says the USB logo should be facing up, so you should always try it first with the logo facing up. Not every device follows that standard and not every device has a clear top/bottom, but this really cuts down on the proportion of failed attempts.

No way! I didn't know that was part of the standard! Very useful "trick" indeed, unless of course, the USB port is placed vertically...

The pattern on the aluminum of the plug is also helpful in cases of predictable slot orientation (like a laptop, except a Dell Latitude from back in the day that had upright connectors on the back unless I'm misremembering). The side without the seam down the middle and instead a tiny rectangular cutout center but slightly lower than the other two cutouts, should face up. In the dark, the seam can be felt by lightly scraping with a fingernail.

The holes face up, like the eyes of a sole or flatfish.

One trick used to be the UBB trident logo (embossed into the cable) always faced upward when plugged into a USB port on a computer.

Sideways ports may be a crap shoot I'm not sure if their orientation is standardized. And I'm not sure about modern USB version if that's still the case of logo faces up.

This gets you down from 3 tries to 2

lol ty, this got me