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Partial breakthrough, but it's making me question my sanity even more...

Drive now works with 100% perfection, as long as I do NOT have a keyboard plugged in.
Doesn't matter WHICH keyboard (I've tried 3), nor does it matter if I plug the keyboard into the hub or the Pi itself.

And once the Pi is booted, drive running perfectly, if I plug in a keyboard, the drive instantly disconnects.

So either I'm going insane, or the drive's USB/SATA interface is bad in some wonky way.

Well, welcome to the whacky, weird world of the Pi

Does the drive have separate power and USB connections? Or does it get power on the USB connector? If it's all on the USB connector you may need a Y cable (Or if you can, make it yourself)
Feed the drive from a separate power supply if possible, ie not through the USB hub. Or the same supply, but separate from the hub. If it's a 3.5" drive, it should have it's own 12V/5V supply. A lot of 2.5" drives draw more current than a hub can (theoretically) provide while spinning up and depending on how everything else gets powered, cause a temporary drop in voltage. Just enough to create "issues".

MaxK1 wrote:Well, welcome to the whacky, weird world of the Pi

Does the drive have separate power and USB connections? Or does it get power on the USB connector? If it's all on the USB connector you may need a Y cable (Or if you can, make it yourself)
Feed the drive from a separate power supply if possible, ie not through the USB hub. Or the same supply, but separate from the hub. If it's a 3.5" drive, it should have it's own 12V/5V supply. A lot of 2.5" drives draw more current than a hub can (theoretically) provide while spinning up and depending on how everything else gets powered, cause a temporary drop in voltage. Just enough to create "issues".

Nope, powered by USB. Luckily, the cable is the Y type. So I can wire that second connector (pins 1 and 4 I'm assuming) straight to my power input?

Yup - I have rigged mine up that way (I also put a cap or 2 across the power supply to at least lessen power sags when "hot plugging" various things) Seems to work well.

Finally had a minute to patch the cable. It's working perfectly now!