You should be using pageant to store the secret ssh keys, and you only need to unlock the key on reboot/first use.
Ssh agent will manage your ssh keys through windows registry windows login process.
Also if you use wsl, you can access your ssh keys in wsl from the windows ssh-agent via npiperelay
For me, the stakes are very low. It's my windows "gaming" machine, and has access to a few low-value hosts.
Otherwise I'd invest the time to learn wtf is pageant ;D