Ok, here goes...JMHO, and I hope no one flames me for this...
I do believe in the "cry it out" process. With my youngest, I was getting up with him 4 - 5 times a night and holding or breastfeeding him. I also had a toddler, so this was waking him up too. Not a pretty sight!
Anyway, at 10 months, I bit the bullet and let him cry it out. Thankfully he was like the kid in the textbooks...cried for about a half hour...then less each night...not too bad really. He was sleeping through the night in about a week.
On the other hand, my first child was MUCH more difficult in this area. He could cry all night. It was just too difficult to let him go through the process...so I didn't. As a result, he didn't sleep through the night until he was 2 1/2 or so. In retrospect, I do think he would have done just fine if I had continued the "cry it out" process. It may have taken a while, but he would have learned to put himself to sleep (which is, IMHO, a good thing).
It is a very personal choice and no one can tell you what is right for you and your child. I just wanted to share my view and wish you the very best in whatever you choose. You obviously sound like a caring, sensitive parent...I'm sure you'll know what to do.