C.D.
I can tell by your earlier request for advice (from when your son was six months younger) that you have got a seemingly stubborn little guy there with some sleep issues. Sounds to me as though six months later, he is still trying to get some extra reassurance from you. You have all the evidence in the world to see that the cry-it-out method is not working with him. Most children this age will regress back to old habits (that you'd expect they'd grown out of by now) so they can get what they needed that they didn't get when they needed it. You can take action now, or have a two year-old waking you up in the middle of the night just when his little brother or sister has finally fallen asleep. I do believe it is time to try some cosleeping so you can strengthen his feeling of security. After all, cosleeping is a wonderful way to transition a little one that age into their own 'big boy bed'...and it seems you'll be needing the crib soon anyhow, so why not give it a try? You'd probably only have to sleep like that for a month before you started him out on his own bed. Make a big deal about the big boy bed and get a reward system going that works for all of you. This link will take you to a very helpful source http://www.askdrsears.com/html/7/t071100.asp
Congratulations on your new baby!!