Ford 860 goes from bad to worse

So I posted earlier this week about a electrical issue that ended up as a condenser issue. Put a new one on and it started right up idling with ease. Used it maybe an hour, and the issue started up again. Assuming I got a junk part from TSC, I went and got another one. This time, I'm getting no spark, BUT EVEN worse I start noticing a black oily liquid coming from the 2nd cylinder... Didn't see anything in the 1st cylinder and I'm not noticing any radiator issues so I assume it's not just a head gasket.

Question 1: Are there thing that cause the condenser to go bad?
Question 2: Can a guy with decent mechanical skills figure out a piston/valve seal issue and fix it solo, or is that too ambitious?

Not sure what to do. I've never rebuilt a motor before and I'm sure it's not worth it to have someone else do it. The tractor itself also needs a new gas tank valve and carb work, could use new front rubber. 3pt. has a few minor issues but is functional.

I use it for plowing so I need to get this figured out before winter hits here in Wisco.

My wife doesn't want to hear me complain about tractors so I'm coming here ramble and vent . Ug.

New condensers have been known to be bad right out of the box. . Perhaps your 2nd new condenser is one of those. But find out if you've got good electricity at the small wire at the distributor. If you do, then the new condenser is likely your problem. Also check that this small wire isn't grounded where it passes through the distributor body.

I start noticing a black oily liquid coming from the 2nd cylinder. Didn't see anything in the 1st cylinder and I'm not noticing any radiator issues so I assume it's not just a head gasket.

Click to expand...

Where is it coming out? Did you pull the exhaust manifold to actually see it coming out of the cylinder, or is it oozing out from around the manifold, or from the seam between the block and the head?