I agree with you on both counts (not one to let the child "cry it out" and not wanting to wake up big-brother).
First: If he's teething, I'd use Motrin at night...it's supposed to last 6-8 hours instead of 4 like Tylenol. (And keep using the orajel until the motrin kicks in.) Ibuprofen was initially developed to help with dental discomfort anyway.
Second: If you aren't doing so already, with the bottle he has before bedtime, put about a spoonful of cereal in with his bottle (make sure you have a y-cut nipple, or be willing to make a small slit with a knife).
Third: Get some Mylicon and add that to the bottle too. Our oldest was about 6 months when we realized she was having gas issues and the Mylicon took quick care of that.
Fourth: Is he sleeping on his back or on his stomach? We got grumped at by our pediatrician's office because our oldest would NOT sleep on her back (absolutely wouldn't do it); SO, we would lay her down on her tummy, and she'd sleep easily. BUT we were very diligent about checking on her a lot, there weren't pillows in her crib or things that could obstruct the flow of oxygen somehow, and she did sleep in our room for a long time...but it was something to consider. Our second daughter had no trouble sleeping on her back, but we couldn't beg or bribe our first to sleep on her back.
Those should help him sleep better - it definitely helped with us.
For what it's worth - and good luck!!