Progress! Yeah, I think I scrubbed at the game boy for about a half an hour before I could get a reliable connection. My guess is that the handshake still isn’t quite completing correctly, and maybe more scrubbing would work? It would be really helpful if you had a known-working cartridge with which to test. Beyond that, though, I would have to do subs Google sleuthing to find anything else.
I will say, though, that your screen seems fine, so it’s probably not that.
The oldest system I have would be the NES. My brother received it sometime before I was born. I’m just holding onto it for him, though - it doesn’t get played right now. I actually intend to clean it all up and retrobright it before sending it back to him… eventually… The oldest system I have that still gets occasional use would be my Gameboy Color, which I received, with Pokemon Red, for Christmas when I was 8 or 9. Unfortunately, I need to find a better plastic polish, to take some light scratches out of the lens, and until I do, it will remain disassembled… I’ve also been contemplating using the board for a complete boxypixel overhaul, but there’s something about still having my full original GBC that I’m having a problem getting over…