J.V.
My son was exactly the same way! We co-sleep, so I know that makes our situation a little different, but here is what worked for us....
To get Conner used to napping, I got a good wrap (gysymama) and wore him. I'd play with him, feed him, wrap him up, bounce him, and he'd fall asleep. Once he got used to napping, I laid down next to him in bed, nursed him, left a teddy bear that I had squired milk on, and left. If he woke before an hour, I'd lay back next to him and nurse him until he fell asleep again. After a few weeks, he stopped waking and was sleeping 2ish hours.
A good wrap makes all the difference because they are warm and tight on your body. Moby is a cheaper version that works well.
As far as the crying, I'd be very careful with that. They aren't sure the long term-effects, and honestly, who likes to fall asleep crying?? I will share a few links with you on the possible long-term effects of leaving a baby to cry and/or long-term crying. I hope they help you.
http://www.naturalchild.org/guest/pinky_mckay.html
http://www.askdrsears.com/html/10/handout2.asp
http://www.sleepnet.com/infant3/messages/534.html
http://parentingfreedom.com/cry-it-out/
One more thing. The book The No Cry Sleep Solution by Elizabeth Pantly is full of amazing tips and ideas. It is a lifesaver!