Transitioning baby to crib/pack n play-HELP!

Has anyone else been here with their baby? Our 9 month old slept in his bassinet and pack and play until he got a cold and ear infection around 6 months. We let him sleep with us propped up in the boppy pillow because he was so stuffed up and didn’t want to lay flat with the ear pain. He is 9 months now and screams relentlessly to the point where he has a hard time catching his breath if I even set him in the crib or pack n play. I tried a couple weeks ago to see if he would calm down after a bit and he wouldn’t calm down! We have tried making the crib fun with toys so he would get used to it, put him in there asleep (he immediately woke up), put him in there tired. Nothing works and I am at my wits end. I don’t feel like it’s safe for him to sleep with us, especially because he started crawling.

It’s so hard to let him cry, and even worse because my husband and I both work full time and desperately need our sleep. He is a terrible sleeper and has never gone a full night.

Anyone else in the same boat? Any advise? Does it get better?