It's going to be different for every mum and child.
DD was ELCS, it took 4 days for the milk to come in and I really struggled, til a wise older midwife quietly gave DD a 2oz bottle as she said the milk was coming in but DD was soo hungry and on the breast constantly I wasn't building up enough to feed her at that point. DD was cup fed overnight in the hospital nursery as I was exhausted.
7am the next morning, my milk supply had well and truly arrived and DD latched on no problem, and didn't look back.
DS was born nearly 4 years later (VBAC) and he latched immediately, no problem. In his case the midwife suggested altering his feeding position a little, which really helped things along.
In both case I never had cracked, sore or painful nipples and fed for ages with both.
I think I was lucky. I certainly can't tell you if it was anything I did that made it all go right.
This is in contrast to my mum, who bottle fed both me and my brother. She claimed it was because she had small breasts so couldn't feed. I am sure the real reason is that she had, and still has, some very weird ideas about bodily functions.