We offered two sides until she was 3 months old from memory, might have been a bit longer. My understanding is its important to offer both sides to get your supply established, which I believe is around the 3 month mark? We use to time the feeds so 30 min each side with a few burps inbetween.
I always allowed DD to comfort suck coz I was so worried about lack of supply and figured any sucking is good sucking. The discomfort of BF settled after a while for me (we had some big attachment issues).
As for the dummy, I know people who have given their babies a dummy from birth and it completely messed up their feeding. I know others who's babies seemed to be clever enough and it never caused an issue between dummy and feeding.
I never wanted DD to take a dummy, and fortunately when given the choice she didn't want it.
I wouldn't offer one until your supply was well and truly established, it might be fine or it might cause more harm than good in regards to supply. You'll probably have a lot of people trying to push into dummyhood so it really depends on what you're happy with.
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