Hi Debbie,
I completely understand what you're going through. I used to bf my ds to sleep up until he was 4 months old. I would suggest sticking with the bfing longer (until you're ready to give it up, not because you think he's dependent on it). You can eliminate the sucking to sleep association without taking away breastfeeding. I wouldn't recommend letting him cry it out - it's not the Baby Whisperer way and it doesn't sound like you feel right about it. Do what feels right for you and your family.
I don't think it's too late to wean your little guy off of the nursing to sleep. It may take longer than it would earlier on, but it is sooo worth it. I can now lay my ds down awake and he falls asleep by himself.....I never thought I would get there, but I did! He's also sleeping through the night! That was something I used to dream about as I was laying in bed nursing him to sleep yet again! You just have to do it VERY slowly and gently.
I used the Gentle Removal technique where you remove the nipple just before he's sleeping. If he fusses, put it back in and count to 10, 20, whatever. Try to remove it again. Slowly, you can start taking the nipple out earlier and earlier so that he learns to not fall asleep with it in his mouth. I probably haven't explained this very well, so check out this link (it's from the Night Wakings forum)....
http://www.babywhisperer.com/forum/gentle-removal-plan-vt24669.htmlI would definitely reccomend this method! You could check out
The No Cry Sleep Solution by Elizabeth Pantley....that's where this method is from.
You could also try pick up/put down and use the technique that Tracy suggests for older infants. Check out the pu/pd board for info.
I learned that consistency was the key. Whatever you choose to do, you must be consistent for it to work and so that your little guy knows what to expect. If you keep changing the way you react to his wakings it is too confusing for him. Things will get better, I promise!
Good luck and let us know how it goes!