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If you're planning on using plain Debian and the challenges that come with it, you probably should start with one of the pre-built images from the Debian foundation. You can mount the root partition with either a running linux box or WSL2. Then you can chroot into it to setup the wpa_supplicant.conf in the /etc/ folder and ensble sshd.
Thats something like what I'll be trying. I am on a linux laptop so I can do all that.