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The 2295 will not be 0.030” dome, unless someone milled the dome down. The part number should be on the piston. The 2295 has a 2.030” compression height. If it’s a 2295 milled down to 0.030”, the CR will be less than 10:1, and maybe close to 9:1 depending on head volume, deck height and gasket...
And then what will you do with that information? Sounds like validation.
If you were not looking for validation you would put the cam in and go, not posting to see if anyone has used it.
It would be odd for oil leaking into one intake runner on each side of the motor (#3, and #4 cylinders). Usually adjacent pairs leak. Sometimes 2 cylinders, sometimes 4.
As stated earlier, a leaking head gasket will not present oil as shown in this case. Other plausible explanation have been...
I was given for free a 1958 Chraftsman RAS about 25 years ago. Truly a beautiful piece of equipment. I did nothing to it. Used it a bunch, then gave it away 3 years ago, still needing nothing.
If you want it, go for it. If the plan is to work on it to flip it, your time would probably be...
I think a lean cylinder can cause this condition. The plug gets black because of mis-fire due to the lean condition.
But it does seem like other things are going on too. What cylinder? 5/7? Maybe something gone wrong in the intake tract causing the lean condition?