D188 head woes

[Eric A]

Had our Farmall 504 with the D188 motor blow a head gasket recently. It’s happened before, just did a quick and dirty head gasket on it 1.5 years ago. 
Now I’m looking to fix it right. It’s manifested in a leak from #3 into the cooling system. Bubbles in the radiator. I retorked the head to 120 ft lbs and that helped for a bit. But yesterday when I was mowing I saw that I had exhaust gasses escaping out the side of the head from that #3 cylinder.
Removed the head today and this is what I saw. #3 has an unusual amount of carbon build up both on the edge of the liner lip and on the head also. But I saw no flaws in the block or head otherwise. 

Things I’m wondering about. When we changed the head gasket 1.5 years ago it was quick. I don’t remember exactly but that carbon may have been there and may not have gotten cleaned up when we put it back together. Could it be that the carbon kept the head gasket from sealing properly? I also just reused the 60 yr old head bolts. They could have stretched? 
Other thoughts are a warped head. I’m planning on taking it into a machine shop tomorrow to be checked and gone thru. I was thinking that if it was warped that they could mill it flat. But now that I have the head off I’m not sure that possible. The combustion chamber has no dome like a gas motor would. I don’t know how much you could deck this head. Am I wrong about this?

So what’s your thoughts? I’ve got really good new gaskets ready to go from Olsens gaskets. Thicker and more substantial than the old one. I also purchased new super stout head bolts. Going to have to wait to see what the machine shop says on the flatness of the head. How would you guys handle this and fix it right?

Also what’s the right tool for removing that carbon without damaging the block or head? 
 

[rustred]

thats quite a mess u got going on with that cylinder, the coolant has been leaking in there for some time to have it all pitted like that.  definitely needs machine shop work.  the  valves will be removed and the head soaked and cleaned. then resurfaced most likely will need .015-,020 shaved off.  then depending on the valve seats they will either be replaced as needed. dont think that head has seats so they will cut those out and install new seats and have them installed with the correct valve recession spec. ideal would be .005 recessed to keep your compression up there.  once they get down to around .040 its  new seat time anyhow. plus the valves will be checked if they are still serviceable. plus guides and valve springs and keepers will be checked. you should be coming out of the shop with a totally rebuilt head, no half azzed jobs for this head. plus you never ever drag a head as i can see with the marks on the valves, especially a newly resurfaced unit as that means u just screwed up that job! all carbon must be meticulously clean everywhere on the block. use a razor blade or a gasket scrapper, making sure not to make any scratches. i use permatex high tack spray on my head gaskets all the time . many use copper coat also.  a warm up for an hr. after started and then the final retorque and valve setting. these baby engines and  like the 282 will prove your job. and if you thinking just to replace that gasket again your wasting your time and a head gasket.