Ok, I've done some more fiddling with this. I've been trying to do it quicker but between plowing an the extreme cold I have not had much time/ability to do so

I changed the spark plugs. The gap on the old ones was WAY too much, and I'm not convinced that it was getting enough spark. I also found the little rubber elbow on the plastic vacuum line -> fuel pressure regulator was cracked. Got a small length of 1/8 hose and fixed that. Then I pulled the valve cover and cleaned the top end. There was no sludge but there was a decent amount of contaminated oil. I then thoroughly drained the oil (again) and let it drip for a while. I re-filled with clean, fresh 10w30 and a new Wix filter.
With the new plugs and FPR vacuum fixed it runs smoother and fires up quicker. I think the fuel pressure might be a tad low; ~32 at idle, ~40 with throttle. But that wouldn't cause the issue I seem to be chasing.
Something peculiar happened when I had the valve cover off. Coolant was coming out of one of the valve cover bolt holes. I do not think that it should be doing this. Maybe it rusted through, or the factory drilled it too deep and hit a water jacket. Anyways, with the new valve cover gasket and the little bit of RTV that I put in the hole followed by a bolt I do not think it will be an issue.
I'm going to take it for a test drive now and hopefully use it a little more to keep an eye on everything.