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.
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.