Tips for sleep training an 11mo old

I need help from the momma tribe on here! Lol My son is 11mos on the 20th. I would LOVE to hire a sleep consultant but I truly can't afford it. our situation is so unique so it's hard to piece together advice from books and everything and to find something that works for us.

He slept in his crib from 2-3.5mos through the night until the 4mo sleep regression ruined everything 🙄 we came back to bedsharing, had coslept before but he outgrew his little cosleeper so we practiced safe bedsharing. I half assed tried sleep training by without guidance or support it was a complete failure. Our current schedule is inconsistent which makes things harder.

Currently, I do his bedtime routine and then sidelay nurse him to sleep, after a while when I feel he's in a deep enough sleep I transfer him to his crib, 97% of the time this is successful, I'll go shower and get ready for bed and typically anytime between 12/2 he wakes for comfort and I pull him back into bed with me, nurse him back to sleep and often fall asleep nursing as I know anytime I try to transfer him after this wake up he gets upset. Lately like the last week or so he has been waking up at 2/3 am and wanting to play for 1-2 hours and then wakes for the day between 630/7 but is pretty restless the entire time after that 2/3 am wake up.

His naps well it seems he is transitioning from two to one but it's hard, they are also becoming inconsistent which I feel is a result of the 8-10mo sleep regression. His AM nap is around 10/11 am and anywhere from 1-3 hours, his PM nap is usually an hour MAYBE two, but not often and sometimes he doesn't even take this nap.

I work at a family friends kennel, picking up sporadic shifts as I just needed something to get me by while I figure out my next step career wise. The shifts are 4 hours max but the AM shift is at 630 usually done right at nap time so that usually is fine aside from the early wake up. the PM shift is 430, so it runs into his bedtime. Previous to this I had him in bed by 7 every night and he was consistent only woke up at 4 am to nurse and then would transfer back fine.

I just don't feel this is an efficient way for EITHER of us to sleep and would like to implement gentle but firm (if that makes sense lol) sleep boundaries. My very very last resort would be to request only AM or PM shifts to create the consistency but if i can make it work otherwise, I would like to. I don't think that it makes me a bad mom to have to work shifts to put food on our table, even if it causes a bit of a schedule leeway.

I'm a FTM and I'm a single mom, so I don't have the option to have dad put him to bed or anything like that. Any advice would be much appreciated! Tips, what you did, how you did it, etc. TIA

Pic just because, he is very cute in his crib haha