It's nice to see someone else's approach!
Looks great so far.
A couple of questions:
Did you decide on an anchor yet? Another possibility is the top of a valve stem for a fawcet. It has the same thread usually (10-32), and If you knew a plumber, you could get some for free maybe.
Did you hit the channel where you wanted to? That part is scaring me!
That's a long 3/8 bit, where did you get it?
I'll have to get a safty planer for the drill press. Good idea!