Thanks for getting back to me. I think I need to clarify from my last post. The day that I let him cry was a really bad day. I have a 3.5 year old son who is home 2 days a week in the morning who was also home that day. I put my son down for a nap at 9:00am. He fell asleep quickly but was awake after 30 minutes. I then spent an hour and 20 minutes trying to get him back to sleep while he cried the entire time. I was with him for that full hour and 20 aside from a few minutes where I had to help my other son get set up to watch TV. I finally became very frustrated with the crying and the fact that I knew he was totally exhausted and would not go back to sleep. I think he would fall asleep and then the next second wake crying. I left him in his crib so that I could get a break and take a deep breath so I didn't lose my mind. I think he was in his crib for less than 5 minutes and he fell asleep in that time. I did not leave him there by himself for every long. I am not a supporter for cry it out either but if I become overly frustrated it is best to leave him and come back after a quick break.
I do remember my older son getting better after 6 months. It seemed like one day he just magically started sleeping longer for his naps. I know we need to get to that point but its really challenging the second time around.
He will be 6 months on the 11th of this month. He is still waking up once at night usually around 4-4:30am.
His typical day looks like this:
6:30-6:45 wake up
7:00 Eat
9:00 Sleep, usually only 30 minutes. Sometimes I can get him to go back to sleep if not then I spend the till 10:45 or so to get him back to sleep. If he does go back to sleep it usually takes me 20 minutes of my hand on his back and some pu/pd
11:00 Eat
1:00-1:30 Sleep (We have to go get his older brother from school so sometimes we are at the park longer and don't get home until 12:45pm) Same deal as the morning nap. Sometimes I can get him to go back to sleep but sometimes when I do get him back to sleep he wakes again after 10 minutes. Or my other son comes upstairs and I have to get him back to his room and can't spend the full 20 minutes with him. We live in a 2 bedroom apartment with the second bedroom is upstairs with no door.

3:00 Eat
5:00 Sleep
5:30-5:45 Awake
6:30 Eat
7-7:30 sleep
10:45 Dream Feed
4-4:30 Eat
I was thinking the other day that maybe I'm waiting too long to get him to nap and he's over tired and then can't get back to sleep. Thoughts?
We have also started on solid food some as well. Not sure if that makes a difference in how he's sleeping.
I'm also wondering why he is so fitful after his 30 minutes of waking up when I get him back to sleep he isn't staying asleep. Should I stay and keep my hand on his back for 20 minutes? Also, when he does wake up he isn't crying right away. Do I go up and just wait for him to wake up or put my hand on him before he wakes up? I try to wait and respond but I don't know when the best time to go to help him is.