will that cause me problems on a headless server if I get a power outage and need to reboot? I think yes
Maybe I'm missing something obvious, but what is the problem that you anticipate with LVM after a power failure?
Password prompt on boot load. No monitor and keyboard plugged in, and im assuming i cant SSH until LVM password is entered.
Ah, you're talking about LUKS. LVM is just the volume manager.
The standard way is to add an sshd (such as dropbear) to your initramfs so that you can ssh in and run commands (such as entering the root partition password) during system boot.
See:
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