Cry it out

Keep at it. It takes time, and even then day to day might look completely different.
I sat in babies room on a chair for weeks while we sorted out getting him to fall asleep on his own (he figured it out within days, but I couldn’t bring myself to leave 😂).. anytime he got fussy I would give him a kiss and say I love you. Then I moved outside the door and now he just goes into his crib awake and is sleeping within 10 minutes (most days)
Somedays he naps like a champ and other days he’s awake after 30 mins. I find if he wakes up upset, he needs more sleep so I will go into quickly and quietly and hush him / rub his back. He typically does go back to sleep. Sometimes he doesn’t though, so we finish the nap as a contact nap!
All that to say, there are SO many developmental things happening so it’s normal for them to have ups and downs with sleep! Don’t be hard on yourself :) you got this!

thank you sometimes I feel like I’m risking cause I wouldn’t put him down as a newborn and now he cry’s to sleep. I know it won’t physically hurt him but I can’t help but think about how he missing me. I might just be beating myself up

Absolutely! I totally understand! We only did contact naps for the first four months and only on ME! It’s a lot. I actually left the house for the day the first day we started nap training because I knew if I heard him fuss at all I was picking him up.
A big thing that helped me be better about not running and immediately picking him up specifically in his crib is that I spent time figuring out his cries. There’s a big difference between his “I’m being fussy” vs his “I need you now, something is wrong” cries.. once I figured those out it was a bit easier for me to just kiss him instead of always feeling like I need to pick him up.
All that to say, when we hit 6 months (he’s 7 months now) we had 2 miserable weeks of not going to sleep independently. For 2 weeks straight I had to rock him to sleep (not dad, just me) and all his naps were contact naps or else they were lasting 20 mins.
You are doing great!! Deep breaths!

What really helped me was figuring out how long my baby needs to be awake to build up enough sleep pressure. When she's had the right amount of awake time, she usually falls asleep—day or night—within minutes, needing little to no help beyond some gentle shushing or patting.