First of all, HUGE kudos to you for nursing so long AND for not letting your baby cry it out!!
I wonder why you think you're in a pickle? Do you hate nursing or rocking him to sleep, or is a matter of people telling you that he'll never learn to sleep on his own if you don't break these habits?
As a single mom during my first daughter's infancy, I had to do what was best for the two of us, not what society said, and guess what!? It worked out better than anything anyone was telling me to do. I loved the peaceful time winding down at the end of the day, looking at her little face and touching her fine baby hair. It was time to connect after all the hectic stress of the day- and good for both of us.
I don't know you, and I don't want this to come across as judgemental, but so often I don't reply to posts like this because I parent so differently, and so much with my gut, but I thought maybe it would be refreshing to hear that you can actually do it the way your heart is telling you and it will still be okay. There is no rule that says you can't always rock your baby to sleep if you WANT to. The key is, is it best for your family? If you are saying you honestly don't want to, that is one thing... do you get where I'm going?
I nursed my daughter #1 to sleep until she was 3.5 yrs old. Most of society thinks this is absurd, but it worked for us. She only nursed for boo-boos and comfort after about 1.5 yrs, and then only a "sip" before bed. She slept in my bed until she was 3 and then in my room in a separate bed until she was 5. She is now 8 and sleeping in her own bed in her own room quite well. We snuggle and end the night with a story or talk about our day now. It is all about routine, whether rocking, nursing, snuggling, etc. All children crave routine and love before bed.
With daughter #2 who is now 1, I am nursing and co-sleeping with her as well, and plan to let her lead the way and tell me what she needs. That doesn't mean letting your child manipulate you (which I think they learn somewhere near the end of year #2, NOT as babies!) but it DOES mean listening to your heart and your child's cues. (Both my girls woke to nurse during the night until at least 2.)
Best of luck to you and your little one, and remember they grow up SOOO fast!!
M.
Feel free to contact me if you have any questions. I really didn't want any of this to sound judgemental and reading back over it, it does sound a bit terse. I was just trying to get out my story and reply as quickly as possible before my little one needed me. :)