I have a very similar setup to the author, but instead of running Tailscale in my initramfs, I have a Raspberry Pi sitting next to the home server (which is on my Tailscale network) and I use it like a bastion host. Process is something like:

1. SSH into the Pi

2. Issue the Wake-on-LAN packet to boot the server

3. Tunnel that server's SSH port to my laptop

4. SSH into the initramfs SSH server (I use TinySSH), enter the decryption key

5. Wait for server to come up, then access via Tailscale

This is more complicated than the author's setup in that it requires another device (the Pi), but it's simpler in that you don't need to have the initramfs on your Tailnet.