I have enable-ops set to true however the message "The vanilla OP system is disabled on this server. I tried seeing if i could do the autoop perm that failed as well.

If auto-op is true, enable-ops is forced to be false.

Perhaps that's why you're seeing the message? Remember you need to restart your server for any config changes to take effect. :)

Welp, not my proudest moment, but thank you!

No worries :)