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*kool aid man voice* OH YEAH

I'll buy them!

Wow how strange!

Not sure what you're doing to test, but here's what I do:

With the gameboy off, plug in your keyboard.
Turn the gameboy on, verify the keyboard has power (usually the scroll lock keys flash on boot)
Open the LSDJ song
Go into the settings, and toggle keyboard sync off then back on
Go back to the song screen
Just the arrow keys to verify you can move the cursor around

Well, I don't think usb > PS/2 keyboard adapters will work at all with this. You need a true PS/2 keyboard. I'm foggy here, but there is something to do with those adapters not actually converting it correctly to true PS/2. Similarly, it seems like some modern keyboards internally use a usb to PS/2 adapter. I'm super foggy here, but for sure I'd try to track down a true PS/2 keyboard and see what happens.

Power issues could very likely be an issue if the DMG is backlit as well. I know some DMGs have power issues with backlighting alone. That, said, my DMG is backlit and works fine with a PS/2 keyboard, but I have no idea what kind of power the VGA adapter draws.

The X3 literally has a button INSIDE the cart that you can press. It will reset the cart. So what you have to do is save, then press the button, and it will reboot with your save. But if you forget to push the button after saving, it won't actually save. Not worth the risk IMO.

Nice!

Oh yeah, the lockout thing sure, but OP is saying sometimes MIDIOUT isn't even an option?