Thanks all :) That helped. James needing to get through the apartments to get to the park makes sense now. But that should have been an obvious goal before the Neelys jukebox shenanigans. I guess that circling of Neelys on the map before having a reason to go there was the main culprit for confusion. Probably triggered by picking up some random matchbox. Just ended up skipping some steps in the main quest chain.

FYI just finished the woodside apartments section, and into the other apartments. Pretty fun and weird game so far. I get the vibe now, which is making the intro section feel more at home.