Resolved! With the new LEDs and new 12AU7 all of my voltage measurements were spot on this time, and both LEDs lit up. Seeing both of those LEDs light up is probably my high point of 2020 so far haha.
And my Crack built sounds great by the way. I also have the power cord to build and the Speedball upgrade on standby, but I'll spend a few weeks or so getting familiar with this guy before starting on that.
Thanks for all of your help PB, I couldn't have finished this otherwise!
-Tommy