Nap issues with nanny help..kinda long but help

So I am a single mom to a 16 month old boy and a teacher. I had him sleeping in his crib for the most part on my maternity leave (first 6 weeks) but when I had to return to work as the sole provider I ended up co-sleeping. It was so much easier to cosleep and breastfeed. A mid night wake up went from an hour in the glider to 5 minutes max co-sleeping. My work like relied on me getting enough sleep.

Last school year, my mother babysat and started holding him through his naps. Once I was on summer break I also kept to holding him for naps and continued co-sleeping at night.

Because of other reasons my mother couldnt watch him this school year and the day cares in town were booked so I set him up with a baby sitter. She is a distant relative close to home and has a child the same age. I pay her less than a daycare but almost the same amount as my rent to watch my LO while teach.

Starting this school year I transitioned out of breastfeeding. It took about 2 months to fully stop without crying. I also got to where i could hold him for 5 minutes and lay him down on the couch or bed to take his nap. Putting him into the playpen nor crib after his nap has been an issue. As soon as he feels him self going down he jumps awake and nap time is over.

The sitter started with 2 naps a day. When it was just mine and her LO he was able to nap fine with falling asleep sitting next to her on the couch with her LO. Then she started taking in more kids. Props to her for handling so many kids.

End of November she asked to work with having an 11am lunch then nap around 1130. I worked with him and he sleeps everyday for me after lunch. But he needs to he held for 5 minutes then laid down.

I also started working on him with his play pen. In the past he would scream bad just attempting to put him in his playpen or crib for any reason. I finally got him to be comfortable to start playing in it.

I was feeling so happy like I was making good progress. It's so hard for me to not hold him when I'm already gone for so long working or grading or coaching (coaching helps pay the bills).

Today I got a message that he needs to nap in a playpen in a room alone with no drink or tv (I watch tv while he falls asleep on me so hes used to it)(and breastfeeding to bottle he still wakes up once a night for a drink so plays down with a bottle). She gave me about 5 weeks to make the transition with him for his naps or she wont watch him anymore.

I understand where she is coming from but I dont know how I am going to make that progress that fast and I dont want to give up co sleeping. I feel like I'm in a lose, lose situation.

I make my kid suffer through rough quick transitions where we both lose sleep and I feel miserable because of the few hours I get with him he will be screaming for comfort that he "can no longer get." To keep the affordable babysitter.

Dont make the transition in time and lose my job because I do not have a sitter that I can affor and then lose our home and everything else.

Or pay for a more expensive sitter and lose my home/power/water/car/ or food.

I love the time I get with my LO and wish I could get more and dont want to give up my moments with him because he will grow up and move out in the blink of an eye..

So I guess I'm asking for any advice on what to do or how to help with the transition... is it possible to cosleep at night and crib train your toddler with a share nanny/babysitter? How can I help transition for naps if I'm working at all nap times besides 1day a week? I really dont want to give up cosleeping... does it seem like it's go to have to go?

-stressed mama