I'm not a huge fan on dosing kids with Tylenol or Motrin, but in this case I always suggest to. If you had a painful tooth, you would take something for the pain. You know? Why make babies suffer when they don't understand why their mouth hurts. Have you made a trip or called the doctor to make sure nothing else is wrong, like an ear infection? Especially when you mention that he is waking up frequently, it can hurt a baby to lay down with an ear infection so that could be the cause.
I've worked in childcare with infants for 15 years, so I've dealt with lots of teething babies and ear infections.
I used to nanny for a dentist, and she says that Orajel actually makes teething worse b/c it hardens their gums and takes the teeth longer to come in. Plus, that stuff only lasts for a small amount of time, it's not worth it.
Some people swear by the Hyland's Teething Tablets, so you could try those. I honestly don't think they do anything, but a lot of people swear they do.