With F I feed him to sleep, he wakes after about 35mins, feed him back to sleep, and that's usually him sorted.
Except when he doesn't drop off & starts biting/grabbing me or flailing wanting to play. I get frustrated, put him in his cot to entertain himself till he gets bored & cries. If it's been long enough, I'll attempt to feed him to sleep again (otherwise he'll puke everywhere & need full pj/bed change, and start from scratch), or DH and I take turns to pace with him till he either tires himself out or persists long enough to feed again.
There's no way he'll sleep happy without boob. Without boob (whether in the car/pram/sling) he always cries as he drops off. If he can't fall asleep he gets angry = vicious circle.
It's a bit wearing, really. So I'm feeding him to sleep for as long as it works. Only problem is that no-one else can do bedtime. I'm not overly worried, I want to do bedtimes when I'm back at work, and presumably it'll all change with weaning anyway. I can't see myself having to BF a 14yr old to sleep!
He finally pood just before bathtime (fed him with him sitting upright facing me, with him sort of squatting in my lap. It seemed to help!). But he still wasn't happy. Gave him some calpol (teeth? tummy?), and he slept for an hour before waking for his second bedtime feed.
Hope he sleeps through till 4 now. I need to work!
Good luck Star, I'll be thinking of you.