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This engine will burn [lots] of oil if the piston-to-bore clearance is any more than 0.0015" (one and one-half thousandth of an inch). They were originally bored to have less than half that much, around 0.0004"-0.0006" clearance. As soon as this clearance exceeds 0.0012" the rings cannot hold back the oil anymore, and it starts collecting on top of the pistons because it cannot burn away fast enough. Then things get smoky.
Others above mentioned another real important thing: cracked valve guides. The tips of the guides can become cracked during reassembly if the rockers are not held up while the top cover is being installed and then the bolts are tightened: they will tighten down OK because they crack the valve guides by pushing the valve stems out of the way(!). This is quite common when someone isn't careful to watch for it.
So, it looks like you need at least new oversized pistons and rings and a proper bore job, for starters. Tell your machinist that you want 0.0004" piston clearance (that's 4 ten thousandth of an inch) and if he balks at it, find another machine shop. Otherwise it WILL burn oil on reassembly, from Day One.
Also: while they are working on the cylinders, tell them you want the top of the cylinders milled off 0.010" (ten thousandths of an inch). This is necessary because all modern head gaskets are now that much thicker than OEM ones were, which lets the 2 oil passages through the head gasket leak big time, making a very oily engine. Contact me with your address (PM me) for a pair of thicker O-rings that replace the too-thin ones that come in gasket sets today: there's no charge, and it can save your rebuild from being an oily failure.
While that head is off: remove the valves from the head and look very closely at the tops of the valve guides: see if they are cracked. They may be: if so, then check to make sure the valve stems are straight, because if they cracked a guide, they probably won't be straight anymore. Then you'll have to replace the guides and do a full valve job, too.
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What’s the correct tool to mesure the clearance? I figured the feeler gauge wasn’t it but I’m a carpenter by trade so my fine measuring tools are city blocks in comparison to a machinists.
I’ll have to give the entire valve train a very close look and see if I can find anything,
Thanks for all that info, is there a machine shop you guys recommend, I’ve got a buddy that works on cars and he said he’s had a bad experience with my local shop and that I should ship it off to someone who specializes on vintage engines.
Also thanks for that offer on the prints I’ll definitely pm you here in a bit!
One other possibility for leakin, but not burning, oil is the rubber pucks between head and valve cover, aparently there was a batch of undersize ones a few years back
That’s interesting, the ones I got with the kit seem to fit fine but worth taking a closer look.
So when I got down to it, there were 2 broken head studs, .... I replaced the head studs with a very large helping of heat, pb blaster, and patience, swapped them with the carbon steel ones on 4into1.com.
Where were the 2 studs located? Near the 2 and 3 cylinders?
They were C4 outside front and C2 intake side and outside of that cylinder if that makes sense
So only cylinder 2 and 3 appear to have problems? Your clearance of less than .03mm (.00118") should be OK, but a feeler gauge isn't the best way to check this. 
The top piston ring is for compression, the second is an oil scraper, and the third does most of the oil control. You can have good compression but poor oil control if there is an issue with the 2nd or more commonly 3rd ring.
If oil is coming from the intake guides, it will be worse when coasting in gear with the throttle closed, due to the high vacuum in the intake port, and the smoke will increase a bunch when the throttle is opened up, burning the oil that's accumulated in the combustion chamber. If the exhaust guides are leaking, the oil getting blown into the hot exhaust burns and smokes, but the oil doesn't burn in the chamber like with intake guides or rings. Is there evidence of oil burning in the chambers, like deposits on the spark plugs?
Interesting you say that, I noticed that at idle is smoked a ton but when I give it some gas it goes down significantly to none or almost none. Could be intake valve leak.
Another thing, I’ve got the 3 piece oil control rings on all the pistons, from my understanding those are bidirectional cause I could t find anything marking on them indicating orientation direction.
It definitely seemed like there was oil burning in the chamber of C2 and C3 but I also had oil in the exhaust, c3 plug just had carbon build up but c2 plug had oil on it for sure.
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