So DS2 is 3mo and since about 3wks old he mostly naps in the sling either at home or out and about. This is mainly as he hates his buggy, it leaves me hands free to deal with DS1, and because I simply haven't got him into the habit of napping in his crib.
On mornings that DS1 is at nursery (2 days a week) and at weekends when DP is around I can get DS2 is sleep in his crib. I bfeed him to sleep, let him sleep on me for an hour (yes - if I transfer him before that he wakes up) then I move him to crib and he'll sleep for another couple of hours.
This is a fairly laborious routine and one that is can't do when I have DS1 as even Peppa 'toddler crack' Pig won't keep him occupied for that long. Also I can't seem to bfeed DS2 to sleep at other points of the day so his other naps are in the sling.
In the perfect world if love to be able to put him down awake for his naps and let him fall asleep on his own so I can attend to DS1 without being physically encumbered by (a beautiful and adorable) 15lb weight 
My question is this - I know there are plenty of ways to gently get him to go to sleep on his own over time BUT do I need to also implement a strict nap schedule/routine for this to work?