Hi, I was just wondering about the pain, my dd would also wake in the middle night and be hard to settle when teething but we discovered that if we gave the pain meds before the last lot had worn off by dreamfeeding them with a bit of milk the pain would not get to the stage of not being able to get back to sleep. It is like when I have period pains when I go to sleep, if they are mild and I skip the piankillers they can wake me in the night and if I then take meds, they can take ages to kick in and take the edge off, but if I take them before sleeping I will probably sleep through. Also remember that even if teething pain has calmed down a bit by the early hours even a niggley pain could be keeping DS awake because he has had most of his sleep, I used to set my alarm for around 4am and give dream meds, if you try this and he sleeps longer then you know it is teething, if he is still waking then you know it is routine.
When my dd went to one nap she only ever used to sleep about an hour so we catnapped for a while, just 20 mins 4 hours after wake up, in the pushcair walking around the streets! When it started getting dark early I just put her to bed instead, she often went to bed between 4.30 and 5pm and would sleep through until 7ish! Until this year her bedtime at 4 years was still 5.30pm and now she goes to bed around 6pm. Sometimes even what seems like an EB just isn't early enough when a LO is OT and most LOs need shorter A times when sleeping anyway so OT can build up very quickly.
I just read that you are anck at work, does this mean you are with DS less? If so he may well be missing you so wanting the boob at night, just a thought