I am no expert, but your LO sounds in some ways like mine when I first started BW, same age, too. I found it helped to slowly move from ESA to EAS. I first put a small gap between the daytime feeds and the naps - 10 minutes maybe, and then worked on increasing it slowly. So for a long time we had more of a SAEAS pattern. DS still often will not eat right after waking up, but I don't feel it's a problem as long as he does not feed for naps. I think of it like this: in between naps he has an awake period which is for playing and eating, as long as the eating is not happening right before sleep. With this more flexible 'routine', I could watch him carefully and figure out whether he was ready for the 4 hour routine (he was).
As for self-settling, DS doesn't, I feel your pain. I am trying to change sleep associations (he used to be carried in a sling and now he goes in the stroller) hoping that a new, less established association will be easier to break. This might just be a fool's hope... maybe someone more experienced will weigh in on that.