Hey OP
I'm by no means an expert but I can totally relate! My DS is 15 months and 6 months was when we ditched the dummy as, like you, every time it fell out, he woke up and cried. So I didn't find it the life saver others did!! Sometimes it was 20+ times a night.
I agree about introducing a comforter and this massively helped. It was also this age that naps started to increase from max 40 mins to nearly 2 hours as they're able to link sleep cycles.
Below are the steps we took. I can only offer this along with a caveat that one rule doesn't work for everyone!
Bedtime routine. Consistent every night and milk given before a story, bath etc.
We introduced a singsong rhyme that became associated with sleep. Now, whenever I start to sing it, I get yawns from DS. We pick up the comforter, cuddle with DS, draw the blind and sing our song.
I put DS down with the comforter and sit in a chair right over the cot so he could see me. I put my hand in the cot and stroke, soothe, hum or shush. I didn't this for 1 minute. Then took my hand away and shushed/hummed/use voice to comfort for 2 mins. Then put the hand back in for 1 minute...then took hand away for 2 mins. I repeated this until he was asleep.
First night took 30 ish mins and he didn't get too upset.
Second night repeat. But, if he didn't get upset and need it, I didn't put my hand in but just gently soothed with voice.
Third night I moved the chair back so he couldn't see me. I only got up and went over to put my hand in if he needed it. But I kept up the shushing and humming if he got upset
By night 4 I just sat in the room silently til he was asleep and didn't need to intervene
Alongside him being able to get to sleep on his own, it coincided with him not waking. I could almost draw a graph linking the two.
After a week I was able to just put him down and leave. I also found that picking him up just made it all worse and when I put him back down again, he almost had to restart the whole calming down process.
I used the rhyme and same technique for naps and his naps also slowly increased.
As I said, some methods work for different babies but the key is to be absolutely consistent!