Hi,
as I don’t have that OLED board, I can only guess a little bit.
I am using similar or same breadboards and wires. I have encountered bad wires, with no connection at all. It took me a while to find that out, because I had believed, that a wire is a wire…
Some other thing to consider is, that the Oled might need a proper reset, which is done by power up, so it might need unplugging the Daisy. Also it might need some more time to power up, so a delay might be necessary, before sending commands to it.
As 5V tolerance and SPI is not needed here, it might be the best way to buy a cheaper display without these features.
I tried adding a Delay. Good idea but it did not help. I am beginning to think there is an issue with my Seed.