Dd used to self settle, but it didn't make her sleep through the night. The only thing that improved night times was night weaning her at 18 months (I was pg)...but then I had to give her bananas in bed because she was so hungry! Some babies need constant food and dd was always a very frequent feeder (and still is, although now it's hard finding a million nutritious snacks a day).
Dd will settle without a boob now, but we still lie down with her. It's easier when they're bigger and you can reason with them a bit more.
I think it sounds like feeding to sleep works great for you...but you might need to tweak the evening ritual so dh doesn't rev up your ds too much...otherwise I would look at the number and timing of day sleeps so that ds is really ready for bed at night, so he only needs a quick feed.
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