I really have no idea what I am doing anymore.
Sure you do, you are coming to BW and getting lots of love and support.
I know a few Mommas that have had success with getting their LO on a SOLID routine WITH the early mornings (so 5:30am-5:30pm), getting past the OT, and then gradually moving the day back 15 mins at a time or so until you get closer to 7-7.
It is often very very hard for an OT bub to fall back asleep in the wee hours of the morning because they've had some good sleep during the night.
I would say do a combo of cues and clock - look for his cues for when he looks like he could be ready for a nap, then stretch him maybe 5-10mins more. I agree that an early nap can reinforce the EW so it's a fine line to walk, especially when he's overtired - do you go by what he's looking like or push him a bit more? My gut is to get him caught up a bit more then work on pushing him if that makes sense. Go with the EWs for a few days and really try to get him some solid sleep and then start pushing him more toward your routine.
Is he spirited? I know with my dd that OT is possibly the worse thing for her and her spirited-ness, which is why I kind of take the stance of "Do whatever it takes to get that sleep tank refilled and then start doing the major work." It's not always the popular view here but that's what's worked best for us and our spirited dd.
Also, do you have his room blackened out? Sorry if you already mentioned this but it's late here and I haven't gone back to reread - dd also did EWs until we blackened out her room and it really helped.
As far as feeding, he is getting to the age where you can drop down to 3 BFs, BUT that is a totally separate issue and probably not related. His eating is looking rather decent.
HTH!