After almost two weeks of allowing Max to "cry it out," I would say it's working pretty well! He goes down fairly easy at night, maybe crying 5 minutes or so. And 4 of the last 5 nights he's slept through the night, 8-6 (and the fifth night he slept from 8-4:30). It's been nice catching up on my sleep, although I do wake up a little panicked every morning, wondering if Max is okay.
Naps are a little harder. We've only put him down for nap using the Ferber Method a hand-full of times, and three of the six times have been successful. It's still a work in progress. We're trying to condense Max's naps down to two or three a day (he likes to take 5-6 short naps), which should also help him sleep better at night.
I thought this method would be a lot harder on me than it is. In truth, it's actually easier than rocking him every fifteen minutes throughout the night. Knowing that this is best for him, makes it easier too. He needs to be able to fall asleep on his own, without his mommy endlessly rocking him. I'm glad we took this step, it was a hard choice to make, but it's working well for us. If you're interested in reading more about the Ferber Method,
this is the book I read. It's a quick read and it's pretty interesting. It gave me some good tips for when Max is older as well!