Having problems running headless Pi Zero

[/RaspberryPi]

Hi guys, I've been using rPi since rPi B (2011). I say this not to flex, but to illustrate my confusion that I am no longer able to set up a headless pi with SSH over USB.
I recently wanted to set up my pi Zero W again in a headless configuration as I usually do. It's been a little while, so I have never used Bullseye or the rPi Imager before. At first it seemed much easier than it used to be, but I'm finding it impossible to set up a headless pi into which I can SSH over USB (again, I've done this before countless times: flash image, create ssh file, "ssh pi@raspberrypi.local", and voila!). I've tried Bullseye, Bullseye Lite, Buster Lite, and now DietPi and I can't seem to get in through SSH with any of them.
I've tried adding a wpa_supplicant and going wireless as well, but pinging with "ping -c 3 raspberrypi.local" gives an unknown host error.
After installing Bullseye and running on my rPi 3, there were no problems with booting into desktop using a monitor, mouse and keyboard. I enabled SSH through the GUI and was then able to SSH in from another machine. But upon setting the default boot behaviour to CLI and rebooting (as I want minimal CPU usage for headless use), the pi stuck on boot sequence and I was no longer able to get anywhere at all.
Has anyone else encountered similar problems with the newer images? Or am I doing something severely stupid that I've overlooked? Apologies for the lack error messages for troubleshooting; I honestly haven't got much. My ssh attempts simply sit there and do nothing; the only error message I have got is from the ping attempts.
Edit: I've now installed Bullseye Lite and am running on the rPi 3 with keyboard and monitor connected; no problems there. I've enabled SSH and connected it to wifi (which I've confirmed with ifconfig wlan0) and it downloads updates no problem. However I still can't SSH into it from another machine on the same network. Again, the ssh attempts timeout, whether I am logging into raspberrypi.local or through its IP address.

submitted by /u/notgotapropername
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