Ashley,
I have been going through the exact same thing with my now 8-month old. She was a perfect sleeper from 8 weeks of age until 5 months when she started waking several times throughout the night. She's an excellent napper during the day, eats a lot, etc. I thought her erratic sleep patterns were due to swaddling her in the beginning and then weaning her off but not so much ...
Here's what I've learned:
1). Deb K. also gave me some advice a while back about teething. She was right! We never saw the white spots or tooth buds on her bottom gums but sure enough, one day there was a tooth there and two days later the second one broke through. She was teething alright and the baby Motrin seemed to help. Now she's getting her top teeth (we can see the white spots) and this is disrupting sleep again.
2). To me it seems like the bedtime ritual helps get the babies to sleep but isn't a fail-safe method in getting them to stay asleep. I still do it but on nights like last night, where we took her with us to the Rockies game, she slept great. On other nights where we were on-routine, she may have gotten up 3 times during the night ...
3). My sister attended a lecture by Dr. Harvey Karp (author of The Happiest Baby on The Block) and I had her ask him some specific questions about our sleep issues. According to Dr. Karp, he still recommends swaddling at this age ... although since we already weaned her off the swaddle I didn't want to go back to it. He also highly recommended loud white noise to be played in the baby's room during sleep. This has certainly helped. I have an alarm clock that I bought from Brookstone that has 20 different sounds. I put it in her room and loudly play "Cooling Fan" during her sleep and this has really seemed to help her stay asleep through dogs barking and other sounds made in the house that woke her up before.
4). Make time to wear your little boy out before bed without overstimulating him. Make sure he gets lots and lots of activity in the late afternoon/evening. My husband loves to dance with our daughter to loud(ish) music. On nights where he does this too close to bedtime, I find that she has a more difficult time getting to sleep.
5). "Crying it out" hasn't worked for us and seems to upset our daughter even more. I think every parent needs to try it and see if they can stomach it, if it works for them, etc. At this age, experts agree that a baby will start to understand that if he cries, he will be held or command your presence. I personally believe in the Sears method — that not responding to your baby's cries actually weakens your communication and bond with your baby BUT I do have a limit. Lately, if she wakes in the night before a 5- or 6-hour stretch of sleeping, I have been trying to rub her back, etc., leave the room and come back in in cycles until she calms down. It's much harder than simply feeding her and it takes time. I think of it this way though: if she's awake during the night, I'm awake too so I might as well try something that will help train her to sleep rather than trying to get myself back to bed as soon as I can.
6). I've found that it all works ... and none of it works at the same time. It really depends on the night. The whole thing of "teaching" them to sooth themselves back to sleep is probably one of the hardest things I've encountered so far. When it's 3 am and she's awake for the third time, I know that feeding her will put her back to sleep (and me for that matter). However, I'm really starting to understand how, at this age, issues like separation anxiety and teething really do come into play.
I posted about this very topic a couple of times and I truly understand how frustrating it can be!! We still don't have it 100% figured out but I hope we'll find our middle ground soon!! Good luck and let me know how it goes/what ended up working for you.
E.