Getting LO to nap in crib, help me!

My LO is 8 months old and he's always napped in my arms. He still wakes up 2-3 times a night and NEEDS a bottle, i've tried the paci and he needs the bottle to fall asleep which is a habit I really want to break. The problem is that he drinks it. He drinks 4 ounces and then goes immediately back to sleep. I've tried giving him more to drink during the day so he wouldn't need as much as night and it doesn't work. This is what our schedule looks like

Awake between 7-830am

Play and eat- 9-10

Nap around 1030-12

Naps for about an hour and a half

Play and eat- 12-3pm

Naps again for about an hour 4-5

Play and eat 5-7

Usually goes to bed around 8-830

Wakes up around 1030, 130, 430 ish

I've tried getting him to nap longer and he will only take a bottle when he's hungry. Everytime I try to put him in his crib the moment I set him down he cries and is wide awake. I can't do CIO because I just cant handle the crying. I mean i've let him cry for a couple minutes, go and check on him and repeat. But I've just came to the conclusion that I can't do it. I just need some help from some moms that have been through it. I've never had an established routine, i've tried and then LO started to go to bed either before it was started or 2 hours after I have already done it. I'm just at my wits end, I need something to work. 

Please help me!