LO will be a year in January. He is still eating a fair amount overnight and I feel like he's getting to an age where it makes sense for us to cut that out.

However, I've read that it can be tricky to night wean during winter illness season. LO has been sick a lot (first year of daycare) and I suspect that will continue until spring. He's never been a good sleeper and illness really disrupts his sleep. If he's up sick and hysterical to breastfeed (as of now, when he wakes up at night that is all he wants), I don't have the heart to deny it.

Am I setting myself up for continuous regressions if I try to do it during winter? How did night weaning go for you?