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

Heads were new, but you put the old rings back into their matched cylinder. Did you run a compression check on the motor before you disassembled? The lower #4 cylinder and oil residue on some of the plugs tells me bad ring seal. I've never used the same rings again when pulling apart a motor. A quick hone job and new rings are too cheap to risk having sealing problems. That's just my opinion.
Yes, heads were new, rings were not. Hence my logic for not re-honing. I never did a compression check before, mainly because I was planning to install new rings. But thought I would try re-gapping/checking ring gap, and re-installing back into the same cylinders in the same position, like many of the LS and some Hemi guys do for budget boost bottom ends.

I would agree with you on the ring seal of number 4, except that the leakdown, even cold, showed very good ring seal on all cylinders, except number 6