Trained Crier?

I'm starting to get a little concerned that Kayden is becoming a trained crier like Keilana and this just can't happen. He is waking up at least once a night to get a bottle and refuses to go back to sleep without it. I was up with him for an hour or better last night and the same with the night before, and the night before. I even let him cry for 20 minutes and he kept screaming. He used to sleep 10 hours a night when he was around 3-5 months. I'm thinking that his teething started all of this because he gets fevers, runny noses, etc. Now that I look back, Keilana started all of this when she was teething at 11 months. Last night I had to wake him up to give him some medicine, he felt very warm with a fever. Anyway, do I just let him cry it out? For how long? I fear that he'll feel like I have abandoned him, plus, he is my sweet little boy! After an hour of trying to get him settled last night, I got frustrated and put him in his bed--he cried himself to sleep. I felt TERRIBLE! It only took about 5 minutes though--I can't deal with the sleepless nights like I did with Keilana. She has JUST gotten to the point that she will sleep all night, wake up and go potty but puts herself RIGHT back to bed, and even volunteering her own naps! BUT, it took this long...2 years!