The black hole is normally for the heater line but I guess you can use it for other things. There are adjustable probes that slide in between the radiator fins that are popular now and many like.
Engine vacuum is good for the transmission but not sure for your distributor. I am not familiar with all the 2 barrel carbs but those look like 94's. I do not know if they have a tap for distributor advance use the center one if they do. I'm sure others here can comment on that. On the last Powerglide/Turbo 350 I plumbed I used 1/8 " steel brake line and made it follow the rear of the engine along the right side of the trans supported by 2 or 3 Adell clams and used a short piece of hose at the end. Looked good and functioned properly.
What trans adapter are you using and why the turbo 350 as apposed to a C-4?...Good Luck