When does the crying stop???

So I'm trying to "babywise" my little guy, put him on a nice schedule so that hopefully someday soon he learns how to sleep through the night. Right now our problem though is that he does not like to take naps during the day (or sleep through the night). Putting this baby down awake and letting him cry himself to sleep is not working very well. He just ends up screaming for the whole nap time and leaves mom feeling like a horrible mother for letting her little boy cry for so long!!!! So babywise, I hope that your good fruits start to show themselves soon because I don't know how much screaming I can take.

I took a picture of the ONE TIME that he actually fell asleep from crying, that's right once!!! I don't think that is great progress, but at least it's something right? So next time it's time for naptime and he just screams and screams I can only hope that some day he can figure it out...