High fives for all the good sleepers last night. Positive thoughts for better nights to come for those who are tried today.
Splendide - If he doesn't like being woken when asleep then absolutely don't do it. Trust your instincts, you know your DS best.
Sazzle - do you feed lying down? You can sort of half sleep throughout the feed that way.
Tatty - I understand some babies do just cry when trying to get to sleep. We use dummy to sooth this so don't get the crying. With DC1, when we didn't use a dummy (until she was 20 weeks) we ended up needing to continue to swaddle her until past 5 months old. We used to do this in-cot rocking thing. She's be swaddled and we'd place a hand over her swaddled stomach and rock her whole body side to side while lying down in the cot.
I actually wouldn't recommend it long term because while it got her to sleep at the time, it developed into difficult sleep habits when older. What about helping your DD find her fists/fingers to suck if you don't want to use a dummy?
Dummies are not evil by the way. Just loco nipples for breastfeeders. Great way to sooth and settle a baby as though they were comfort breastfeeding. But I get that a lot of parents would rather not use a dummy.