I think it depends on what your expectations are really.
I'm really laid back so although DS's dates for sleeping alone, sleeping through, self settling, stopping breastfeeding etc were later than some (most?) people would be happy with, it worked for me and I was happy to let him get there in his own time.
Also bear in mind my laid-back nature was probably a factor in these taking longer as I've never really gone with anything more than gentle suggestion - perhaps DS could have been persuaded to reach these milestones earlier, I just didn't see the need.
If you're interested, he fed to sleep always until he was 1, and then usually fed before sleep (coming off the breast to fall asleep) until he stopped recently (at 4). He went to sleep fine for babysitters from about 18 months or so, reliably.
Went into own bed at 2.2. Slept through reliably at 2.5. Has only just started being happy with being left alone to fall asleep at 4.
That sounds horrendous
but for me it wasn't, I didn't mind lying with him until he fell asleep, apart from a couple of bad patches, it's never taken long, max 20 minutes or so? The co-sleeping wasn't an issue for me, and the night wakings were easy because of co-sleeping. When he went into his own bed he tended to either come in with me, or after a few weeks his one and only wake up was before I went to bed anyway, so it didn't disturb my sleep.