Bedtimes

When did you ladies start letting baby put themself to sleep, or sleep training? Or when do you plan on doing that? And how? What does your night time look like with baby? What do you plan on it looking like in the future after you've got some training in?

Right now we have a little routine going that around 8pm lights are out and white noise machine is on for the night and I let him nurse most of the time so he gets enough in his belly to last a decent while, until he falls asleep. Then I put him in his crib all swaddled and cozy, but he wakes up a couple more times to eat before being completely out for the first long stretch of the night around 10-11 (he'll last until 3-6 to eat, then sleep for another 2-5 hours). I'm wondering if when he does those wake ups I should start seeing if he just will go back to sleep or what. I just feel like I have little control over his bedtime, which I'm cool with for now, I just don't know when is a good age to transition.