Wow, I feel your pain. It is so hard to be working and not be able to get a decent amount of sleep. I have a 10 month old, and she has been sleeping through the night (mostly) since she was about 4 months old. I worked with her using the cry out method, and now that she can soothe herself, she rarely wakes up in the middle of the night. If she does, I know something is wrong, and I go take care of her. Usually it is because of pain from teething. The only thing I can do to console her is give her tylenol, a nuk or teether, or a bottle filled with cold water with a slow flow nipple on it, and then rock or bounce with her. I think when he is in pain, crying out isn't a good option.
Around 4 months I started letting her cry for about 5 minutes before I went in (if I knew everything was okay), and then gradually increased the time. Most of the time she goes to bed with just a little fussiness now, and then she goes right to sleep. Sometimes she fights it anyway, or is extremely overtired, so I'll let her cry for about 10 minutes, and then go comfort her. She is always asleep within 15 minutes if I leave her alone, though. Sometimes going in the room actually makes it worse- the crying has settled down, and when I pop in to reassure her, she gets mad all over again and it takes her longer to get to sleep.
What I do depends on the type of cry, and time of day. Depending on the cry, I either pick her up and comfort her, just stand there and talk to her, or give her a nuk or teether and leave. I do let her fuss/cry most of the time to get to sleep, which works, but honestly, I go by the situation. If she cries for naptime, I give her the nuk and teether, and then let her cry it out, because I know she is tired, and she needs the sleep. Your son may only need one nap a day now, so you may want to try that so he is tired at night. You probably want to set a cut off time for when naps have to be finished by as well, so he isn't sleeping until 5:30 and then supposed to go to bed at 8.
I always feed my daughter right before I put her to bed (in her own room) and with generally the same routine at night- bath (every other night), eat and bottle, book, rock and/or bounce for a few minutes, kiss, and put her to bed while still awake. She seems to do much better with a routine, because she knows what to expect. I also have a lullabye CD that I play for her at night, and it seems to calm her down. She doesn't like it for naps as much though, because she knows what it means now! It took her a long time to figure that out, though!
So, my recommendations, for what they are worth are:
-Establish and keep a routine for nap time and bedtime. Lay him down when he is drowsy but not asleep.
-Try skipping the morning nap, and transitioning him to one nap a day. My pediatrician actually suggested this to me for my daughter.
-Make sure he eats food that will stick with him and a bottle right before bedtime so he doesn't wake up hungry.
-If he is teething, give him tylenol, a teether, and cold bottle of water.
-Let him cry it out unless there is something wrong, at least for a week, until he learns to soothe himself. But, since you've had so many changes in such a short period of time, you may want to wait a week before you start to do this.
- After he learns to soothe himself, I think it's okay to pick him up on occasions when he is having a very bad "day", but don't get into the habit of rocking him to sleep every night or every nap. This should be on occasion, and definitely not 3-4 times a night. I know plenty of people think you shouldn't pick him up at all, but do what works for you.
-Don't let him sleep in your bed or in your bedroom. You are trying to teach him how to sleep. Your goal is for him to sleep in his own room, so if you teach him to sleep in your room, you'll just have to reteach him later.
I hope this helps.
Sweet dreams!