Toddler boy is a little over 2.5 years and is still in his crib. He has never been a great "fall a sleeper" and DH and I are worried that transitioning him will mean endless hours of walking him back to his new bed OR staying in his room until he finally falls asleep (we do this now and it takes an hour but are afraid it will take longer if he has free reign of the room).

Baby boy is 4 months and is sleeping in an adjacement room in a travel crib. We must be going through a sleep regression bc he is waking 3xs a night to nurse. He doesn't know how to fall asleep on his own yet so i'd like to start some training at the appropriate time, with the crib that toddler boy is currently in.

So the question become: which should we do first? I'm so confused. DH has a week of vacation coming up in a month...should we do both then or is that just asking for disaster?