The story is always in the pictures when dealing with this old crap that others before you have spent many hours in scruuin' up!
The rig uses only two vacuum fittings/paths. Disregard that entire vacuum schematic I previously posted, that is of no help regarding this vehicle.
One of the parts installed in one of the valve covers is a "cleanable" pcv valve manufactured by ac sparkplug and is not a throwaway. Those are to be taken apart and cleaned/serviced/tested.
The other fitting should be a "flame arrestor", nothing more than a nipple screwed into a baffled area of the valve cover. It's filled with wire mesh like a brillo pad and must also be cleaned by soaking in solvent. That allows clean air routed from the air cleaner to enter the engine when the pcv valve is open to vacuum which pulls blowby gases out of the engine and then burns the vapors through the combustion process.
I've posted many times in these forums regarding the various ways that pcv was plumbed on different IH vehicles, there is no one "right" way to do this, ihc used several plumbing schemes over the years. I've also posted the process for servicing the cleanable pcv valve, couldn't be more simple.
Do a search here using keyword "pcv" and you will find much information. The engine must be able to "breathe" through the pcv system, otherwise the crankcase pressurizes as you have seen and oil will be forced out of every gasket and seal.
The other vacuum path is from the fitting on the side of your Holley 2300 carburetor which goes directly to the vacuum canister on the Holley distributor. That is the "ported" vacuum port for that carburetor as I previously described.
To test the vacuum can, have your mechanic hook it to a mityvac hand-held vacuum pump and test. It must hold vacuum indefinitely, otherwise it's nothing more than a vacuum leak. Those items are not available from any source as new, we've been looking for over 10 years. But we do have on the shelf reconditioned ones that are indistinguishable from new.
That carburetor is a reman from tomco. Tomco went tits-up nearly 10 years ago though sometimes ya still see their parts laying on the shelf. Those carburetors are infinitely rebuildable, I do 'em every day for our customers, one of our top selling items. My x-ray vision tells me that carb is in bad shape internally!