when DS2 was 10 months I started some gentle sleep training. Until that point we co-slept like you from when I went to bed, and I would bfeed him to sleep at bedtime and his naps. He'd wake every 1.5/2hrs throughout the night and I'd just feed back to sleep.
I started by dragging the mattress from the spare bed onto the floor, and at bedtime I'd feed, then put him down next to me awake and lie with him until he fell asleep, essentially ignoring him unless he wanted a cuddle/ssshhing/patting etc. the first time it took an hour, mostly of him trying to crawl off the mattress and play... but subsequent nights he'd just lie there, faff a bit, but eventually drop off by himself, usually tucked into my armpit :)
I wasn't ready to nightwean yet so I continued to sleep there with him and feed him back to sleep when he woke.
After a week or so I 'upgraded' to a pull out bed which I put against his cot, after taking one side off. I did the same thing - put him down awake, and lay next to him until he fell asleep in his cot. There was a bit of protesting the first bedtime, but no real tears and I was there to cuddle/pat sing to him etc throughout. At this point I decided to nightwean too and if he woke before 11pm I'd just feed back to sleep, but between 11pm-5am if he woke I just cuddled/patted him etc. It's all a bit hazy now but he did really well, and within a couple of weeks I'd got him in his cot with all the sides up and he was falling asleep by himself at bedtime and allowing me to pat/comfort him through the bars of the cot back to sleep when he woke in the night. I carried on lying next to him at bedtime and each time he woke at night, but i was able to crawl back to my bed in between. There was some crying, but not like what I expected and he got the new routine pretty quickly. Most times I'd come in, lie down next to him and he;d immediately just lie don and go back to sleep.
At around 13.5 months he started sleeping through the night, and was doing 7pm - 4/5am regularly. It was bliss.
And short-lived....
Last month it all went tits up. literally. He's now almost 15months and wakes every couple hours again and I'm back to feeding him back to sleep (I feed him in a chair in his bedroom - oh how I miss cosleeping...!!). I'm exhausted, my milk supply is back up again to the extent I feel uncomfortable during the day at work, and I'm feeling a bit depressed by it all. I blame thick colds, molars, and who else knows what. I get the whole comfort thing but I do feel a bit annoyed that we;re back here.
Anyway, am planning to start again tonight - will put him down awake, and lie with him until he goes to sleep, and each time he wakes up (will start with 11pm-5am again but hope to gradually extend it to 1opm-6am). Am VERY sure there will be some protesting, especially now that he's older and more vocal, and he will shout at me to GIVE ME BOOB!!!! but I won't leave his side. He;s not ill, he's not in pain, he's not being abandoned or mistreated. he's just not getting milk. I'm offering him comfort, just not the comfort he wants in that moment...
I can live with the crying as I know he's 'just' cross.
Like you, I would always offer my child comfort if they need it, and gentle sleep training is the only way I feel comfortable with. However, this doesn't mean there isn't crying involved. But it's within the limits I'm comfortable with. Like I say, I AM offering him comfort. Just not milk.
Good luck. There is a thread on here called "what worked for us" which I used for DS1 a couple years ago, which helped a lot. Also check our Dr Jay Gordon for his nightweaning plan. It involves slowly cutting back the length of night feeds, so this could also be something you could try. I think its ok to feed sometimes and not others, as long as it's consistent, i.e. yes to feed before 11pm but not after and this is consistent every night.