Considering "Crying It Out"

Okay, so we're considering letting Baby Boy start "crying it out" so that he will learn to sleep longer at naptime and nighttime. He only takes about 30 minute naps when he's in his crib, but if he's laying next to me in bed, he naps for a couple hours. This tells me that he probably needs longer naps than the 30 minute naps he gets on his own in his crib, but he doesn't know how to get back to sleep when he wakes up after 30 minutes. And he'll sleep a couple of hours solid when we put him in his crib at night (with a pacifer) but wake up if the pacifier falls out. He's still "nursing" a couple times a night--well, more like just wanting to cuddle up next to me and suckle from thirty seconds to a minute or two and then fall asleep in my arms.

I've been talking to a lot of blogosphere and "real-life" friends about the issue, and almost everyone recommends "crying it out." They all say it will be harder if we wait until he's older, and I've been hearing "horror" stories of hyper-attachment-parenting parents who never made their kids cry it out and now the kids, at five or six years old, still wake up several times a night wanting mommy and daddy.

I have started getting him on a 3-hour schedule during the day. Today I nursed him at 6:30 A.M. (his usual waking time), 9:30, 12:30 P.M., 3:30, and 6:30. I put him right to bed after the 6:30 P.M. feeding. Is 6:45ish too early for a baby's bedtime? Also, is only five feedings too few for a almost-4-month-old? If/when we do start training Baby Boy to sleep through the night, should I feed him at 6:30 P.M., let him sleep for 3 hours, feed him again at 9:30 P.M., and then make him cry it out/sleep through the night? Will that confuse him if I nurse him the first time he wakes up, but not subsequent times?

If we do decide to start sleep training Baby Boy, Monday would be a good time to start, as Hubby is off work next week and has few other obligations, so if we're both walking zombies for a week, it won't be as much of an issue.

In all of this, we also might "pull the plug" on Baby Boy's pacifier altogether, because he is way addicted to it and needs it (he thinks) to sleep. Hubby and I are tired of getting up a dozen times every night to stick it back in his mouth when he loses it and starts fussing in the night.

There's a steeper learning curve to being a parent than I thought there would be.