Need some opinions on where to go from here...

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So a little update from the past 2 evenings...

Unbolted the rocker gear completely, and ran another cold leakdown test- all cylinders sat with air for a good 5 mins, TDC verified on each one, and all leaked between 5-7%. Pushrods, rockers, shafts all look good (a bit of wear on the pushrod coating with the light contact in the pushrod holes, but nothing bent). Next, I unbolted the intake- of gaskets were perfect, no evidence of water or oil getting past the crossover or through the bottom of the ports. Gaskets are so good they could probably be reused! Cam lobes all look good- all lifters spin as freely in their bores as they did upon initial assembly, and although some wear patterns are further to the side than I'd prefer, overall no concerns with the valvetrain or cam. Next I drained the engine oil into a clean clear windshield washer fluid jug. The engine has a stock pan and had 5 quarts of Lucas SAE30 break in oil- it filled the jug, and then quite a bit more in a regular drain pan. Oil is black and reeks like gasoline, although I'm not sure if it's just me or I actually drained more than I put in this thing. Next, I unbolted the exhaust on the even cylinder bank since that was the one that was really smoking badly from oil (or carbon and gas mixed?)- all the exhaust ports on that bank except for cylinder 2 have the same sludge in the port as what's coming out the tailpipe.

I'm at a bit of a crossroads, as I was truly hoping at this point I would have found more damning or obvious evidence of something wrong. Obviously I have not removed a cylinder head to check the head gaskets, nor have I tested the oil, but judging by its smell, it seems it's contaminated with gas possibly, not water. Not to mention my previous leakdown tests had no bubbling in the water of the rad. A couple of friends with more knowledge and experience than I suggest I put it back together and we wire up an external HEI module to run it and rule out a bad ignition box (even though it's a new but older Mallory hyfire that I've triple checked the wiring and settings on).

At this point, I'm a bit confused of what to do next. What I'm seeing doesn't seem like a typical head gasket issue to my knowledge, and the multiple leakdowns and compression tests at this point suggest to me a healthy bottom end and valves/seals...I've cleaned up the intake for reassembly, but am wracking my brain about anything else I could be missing here before I spend more time going backwards possibly. I've attached some photos just to show some of what I'm talking about here.

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Valve train geometry issue? It can take out the guide and pull oil from the rocker arm area. Pull the bad cylinder head (oil fouled ports). Pull the springs and check the guides. On the other head check the rocker arm sweep across the valve.

I've had aftermarket rocker arm patterns that are hideous. Especially with long valves in the Speedmaster Cylinder Head. Even 273 rockers side load the valve with the long stems.
 
Valve train geometry issue? It can take out the guide and pull oil from the rocker arm area. Pull the bad cylinder head (oil fouled ports). Pull the springs and check the guides. On the other head check the rocker arm sweep across the valve.

I've had aftermarket rocker arm patterns that are hideous. Especially with long valves in the Speedmaster Cylinder Head. Even 273 rockers side load the valve with the long stems.
This has a B3 racing geometry correction kit on it, and the pattern was checked multiple times after mounting it when I was measuring for pushrod length trying to get max lift and the best pattern possible. I guess it wouldn't hurt checking again though since I'm here.

But that said, wouldn't a bad guide have caused a leak during the leakdown testing that I've done multiple times at this point? Or is it possible it has gotten by without showing itself as the problem. I was planning to just go onward and pull the heads and get them checked over, but this last leakdown with no rocker gear and no intake gasket issues has me stumped since I would imagine a leak of some sort would have shown itself at some point here...and with the mention of completely ruling out my ignition, it has me second guessing which direction to head in. I guess I can still pull the heads and then check the ignition after they've been gone through and reassembled...
 
This has a B3 racing geometry correction kit on it, and the pattern was checked multiple times after mounting it when I was measuring for pushrod length trying to get max lift and the best pattern possible. I guess it wouldn't hurt checking again though since I'm here.

But that said, wouldn't a bad guide have caused a leak during the leakdown testing that I've done multiple times at this point? Or is it possible it has gotten by without showing itself as the problem. I am tempted to just go onward and pull the heads and get them checked over, but this last leakdown with no rocker gear and no intake gasket issues has me stumped since I would imagine a leak of some sort would have shown itself at some point here...
I don’t believe a bad guide would necessarily cause a poor leak down. The oil is coming from somewhere obviously and if you’re cylinder sealing up the chances that it’s getting by your rings, it’s not as high as it being sucked down the guide.

Obviously, you’re gonna pull the head off anyway to see that cylinder. And of course you’re gonna pull those pistons out before I broke down that short block I’d be looking at that cylinder head. The other thing it could be a guide bore if those heads have been reworked before. Take a mirror and face it up towards the guide in that exhaust port and see if it’s wet on the bottom of the guide where the stem comes out.
 
I don’t believe a bad guide would necessarily cause a poor leak down. The oil is coming from somewhere obviously and if you’re cylinder sealing up the chances that it’s getting by your rings, it’s not as high as it being sucked down the guide.

Obviously, you’re gonna pull the head off anyway to see that cylinder. And of course you’re gonna pull those pistons out before I broke down that short block I’d be looking at that cylinder head. The other thing it could be a guide bore if those heads have been reworked before. Take a mirror and face it up towards the guide in that exhaust port and see if it’s wet on the bottom of the guide where the stem comes out.
I really don't want to break down the shortblock...if it gets to that point, I have a low mile running 5.9 mag sitting on the shop floor that id swap instead.

Im probably best off removing both heads and getting them checked over. They are speedmaster I bought assembled, and other then checking spring heights and removing the inner spring for break in, nothing else was done to them, so they could probably use an inspection.
You said the oil reeks like fuel. Have you verified that the fuel pump isn’t leaking internally and putting fuel into your oil?
Damn, I never even knew that was a thing. How would I even check that? I just assumed that because the car may have been running very rich it was a carb issue.
 
You're this far in. Pull the heads-its not that big of a deal. No way in hell I'd build it back up without doing that. Even if only for piece of mind.
 
You're this far in. Pull the heads-its not that big of a deal. No way in hell I'd build it back up without doing that. Even if only for piece of mind.
Yea I agree...I guess last night I was just sitting there a bit annoyed that I haven't found something more obvious at this point. Next time I'm out in the shop the heads are coming off and I'm getting them to a machine shop for an inspection.
 
I really don't want to break down the shortblock...if it gets to that point, I have a low mile running 5.9 mag sitting on the shop floor that id swap instead.

Im probably best off removing both heads and getting them checked over. They are speedmaster I bought assembled, and other then checking spring heights and removing the inner spring for break in, nothing else was done to them, so they could probably use an inspection.

Damn, I never even knew that was a thing. How would I even check that? I just assumed that because the car may have been running very rich it was a carb issue.
Would this cause the listed issues though...
 
Yea I agree...I guess last night I was just sitting there a bit annoyed that I haven't found something more obvious at this point. Next time I'm out in the shop the heads are coming off and I'm getting them to a machine shop for an inspection.
I'm not wanting to read the whole thread through. Didn't you mention one of the cylinders was down on a compression test?
 
Would this cause the listed issues though...
What are you referring to? The fuel pump thing?

I truly don't know how much excessive fuel can affect an engine and the extent of "washing down cylinders" can truly have.
 
I'm not wanting to read the whole thread through. Didn't you mention one of the cylinders was down on a compression test?
When it was done hot, yes, because there were a couple of cylinders that weren't firing. I did a cold compression test and the cylinders all pumped withing 5psi of one another.
 

You said the oil reeks like fuel. Have you verified that the fuel pump isn’t leaking internally and putting fuel into your oil?
I had this happen on a small block Chevrolet. It was extremely obvious that the diaphragm had ruptured inside the fuel pump. I find it hard to believe that the carburetor could be running so rich that raw fuel would be dumping past the rings and the engine would still be running. You probably have more than one thing going on that’s contributing to the problems you’re seeing.
 
Yea I agree...I guess last night I was just sitting there a bit annoyed that I haven't found something more obvious at this point. Next time I'm out in the shop the heads are coming off and I'm getting them to a machine shop for an inspection.
It's winter. We've all had builds go sour for one reason or another...

Be patient, inspect, and be diligent with your cylinder bore to piston clearance measurements. Check the ring lands on your pistons.

You may only be in the solution a set of rings, some gaskets and a couple hundred bucks of cylinder head work.
 
I don’t believe a bad guide would necessarily cause a poor leak down. The oil is coming from somewhere obviously and if you’re cylinder sealing up the chances that it’s getting by your rings, it’s not as high as it being sucked down the guide.

Obviously, you’re gonna pull the head off anyway to see that cylinder. And of course you’re gonna pull those pistons out before I broke down that short block I’d be looking at that cylinder head. The other thing it could be a guide bore if those heads have been reworked before. Take a mirror and face it up towards the guide in that exhaust port and see if it’s wet on the bottom of the guide where the stem comes out.

Valves are closed for a leakdown. I wouldn’t expect bad guides to show up in that test.

Is this the thread where the valve stem seals for two cylinders weren’t seated on the guides?
 
Valves are closed for a leakdown. I wouldn’t expect bad guides to show up in that test.

Is this the thread where the valve stem seals for two cylinders weren’t seated on the guides?
He's experiencing fouling in a couple of cylinders on one bank. The O.P. claims that the leak-down is 5-7% on the foul bank and the intake runners are clean any of oil fouling.

He's trying to prove that the cylinders are not the issue, but...there are still some variables. That oil is getting in there somehow. I know J. Kaase had a couple of video's on reversion fouling floating around.

Perhaps he contacted a valve stem seal with a keeper with valve float and split the top of it..?
 
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