If you get it wrong 50% of the time let me substantially reduce that for you: logo goes 'up' for whatever the normal orientation of your device is. That should clear up 99% of the cases.
I had a Cooler Master case where the IO stack at the top of the case had the opposite orientation (logo down). Threw me off forever.
I'm at a point in my life where I've just given up and figure that I'm only going to get it right 1/3rd of the time anyway: Nope, turn; nope, turn; yup.
Eww that's weird, ok in your case you are out of luck. That's pretty strange though, I have a ton of USB-A devices here and they are all in line with the way I outlined. So that's a bit of a surprise but it may well be an exception.
As for the ones that are sideways: the 'bottom' of the case is the bottom of the motherboard, so if you think of it that way it might still work for all but the top side ones.
