The opposite of your typical "Cannot interface with pihole"

Before you click off immediately, Try hearing me out. Obviously I've been all over the internet trying to find a solution to this, But I seam to having the opposite of everyone else.

Started my night off with deciding I should update my PiHole server, no problem right? SSH into the thing and can't remember my password. So I just grabbed an HDMI cable to reset it... But for the life of me can't figure out why I can't get to the terminal?? It's like it's getting stuck booting, But the PiHole API still works just fine.(See pics). I can get into the web interface just fine, But why in gods name can't I get into the physical terminal? I've tried rebooting it with and without my PADD display, Did the same thing. Any feedback would be greatly appreciated.

Pics can be found on my thread over on the LTT Forum:

None of the issues posted are Pi-hole related.
Better luck on the Raspberry Pi forums I guess.
Below a way to reset the shell/ssh password: