10 months resettling issues

Hi, my baby is almost 10 months, we have had a rough road but after gradually withdrawing support at sleep times he now self settles and recently has started sleeping through some nights without a feed. He eats well during the day and day sleep varies but is usually 2 naps around 2 or so hours total. However, when he does wake in the night, usually between 12:30 and 2:30am he takes up to 3 hours to go back to sleep. If I try and settle him in his cot or try controlled crying he will cry off and on for the whole2- 3 hours, I've rarely had the stamina to keep this up and end up picking him up and feeding him by which point he is so tired he sleeps in my arms or I put him down and he self settles back to sleep till the morning. I've found recently that if I pick him up, offer teething gel/Paracetemol/feed ( has had cold off and in for weeks plus teething) then pop him back down after about 30/40 mins he will self settle back to sleep but then wake 30 mins later, it's like he hasn't been awake long enough to sustain a long sleep at that stage, so he's up another hour or so then again self settles back to sleep, there iis quite a bit of crying in between however, i think because he just wants to play and i want him to sleep. My question is when he is better how do I sleep train for these wakings? He can obviously get to sleep under the right circumstances but when he wakes and gets upset he doesn't self soothe easily, I've tried a comforter but he isn't interested, he doesn't have a dummy. I know I've been inconsistent and there will be some crying but I just want to minimize it! Thanks, Claire