B.R.
I totally agree with you- cry it out sucks. Read what I wrote in response to "ever awake 2 year old"- it's kinda long and I don't want to retype it:) While I don't agree with cry it out, I do agree with their reasons- falling asleep is a skill kids have to learn, not something they do naturally. However, abandoning a kid to cry it out violates the trust you have just spent the past 16 months fostering in your child. So you are right not to want to let him cry it out, and don't listen to anyone who says "it's the only way!" And, as I say in the other post, it's not easy or fast, but it will pay off!
One thing, it would help if I knew how he went to sleep at night- does he fall asleep on his own? Even if so, he may have gotten accustomed to falling asleep in the stroller during the day and compartmentalized the two experiences. No more stroller naps! That DOES need to stop.