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Two questions:
Do you have anything between the Pi and Display, like an HDMI switch? Sometimes the Pi incorrectly sets the display resolution if it can't communicate with the display directly.
Did you use the Raspberry Pi Imager program? You can configure SSH and WiFi, before you even image to SD. It's how I set up my headless stuff so I don't have to futz with connecting displays.
No, just an hdmi cable directly between the pi+monitor.
Just downloaded the .img.xz, extracted the .img with 7zip, flashed to a card with win32diskimager.
Any reason you avoided the official Raspberry Pi Imager software? You really can just configure a headless OS all before flashing the SD card. Choose RPi OS lite from the list, then set up your hostname, username, password, wireless and turn on SSH service. Then all you have to do after flashing is plug in power and SSH in. None of this display troubleshooting would be needed.
Because this method has worked just fine for years. It's also how I restore my backups so it's a familiar process.
Configuration was never the issue; I have no problem setting it up manually and switching it to being headless when I'm ready for that.
The display not working is a symptom; the entire device was shutting down, not just refusing to output video unfortunately.
Turned out to be a faulty sd card. New one is now working just fine.