Let me be very clear about this: I do NOT think letting a baby/child cry it out is a good idea. Little people cry for a reason, whether it be hunger, discomfort, or a need to be cuddled, and I think we have a responsibility as parents to respond to those needs. Babies don't cry just because they feel like being contrary.
At the same time, though, I don't see any reason to go rushing in at the first peep. When I put Zeke down for a nap, occasionally he fusses for a few minutes, but usually is asleep within five. If he fusses longer than that (or does the kind of screaming that scrapes your eardrums) I try the cuddle-and-sway routine, which usually does the trick. If not, we scrap the plan and try again later. Maybe this means the laundry isn't done but, frankly, he's more important than laundry.
When we're out and won't be home for naptime, I do a front carry in the Kozy, and he'll snooze in there for a solid two hours.Finally, we usually end up cosleeping at night, which seriously cuts back on the crying and regular waking. Normally, we don't start out intending to keep him in the bed, but often I'll fall asleep when Zeke does, and then Adam just leaves him there when he comes to bed. This is made a lot easier, of course, by having a king-sized bed :)
People sometimes say, "But don't you want him to learn to fall asleep by himself? Don't you want to have a little time for yourself at the end of the day?" Of course I want both of those things -- but I'm not going to push either one of them. I didn't get into parenting to have time for myself, and anyone who does is delusional. Zeke WILL fall asleep by himself when he's developmentally ready to do so (and already does, sometimes). I'm just not that worried about it.
My basic sleep philosophy is this: I don't want Zeke to have negative associations with sleep. I know he likely wouldn't remember crying himself to sleep, and it probably wouldn't cause personality disorders when he's a teenager. That doesn't, however, mean it's the right thing to do for our family. I'll take loving cuddles over leaving him alone to cry, any day.