I haven't worried about getting any of my 3 to self settle.
DS1 still wanted to be cuddled to sleep until he was about 3, but since then he has been no problem. Gets into bed after his stories and goes to sleep around 7 every night. DS2 still comes out and sits with us after stories while he has his cup of milk. If he is really tired he falls asleep cuddling either DH or me after just a few minutes, other nights we can tuck him into his bed after his milk and he goes to sleep by himself. He was 3 in April. DD just turned 1 and still feeds to sleep most nights. I quite like the time I get with her so it doesn't bother me that I can't just put her into bed. I figure she will go to bed by herself soon enough, the other 2 don't need constant rocking anymore.

Just do what makes you happy. They are all different, but they do all sleep eventually.