DS isn't a great sleeper too. Some things we do:

Bedtime routine:
Dinner, In the Night Garden, bath, story, bed. This starts at 6pm and he's in bed for 7.30, asleep before 8. Only worry is when we have to go somewhere with no digital TV (free digital TV, I don't expect people to shell out money for DS!) but at least we can download from the BBC and let DS watch In the Night Garden that way.

One parent does bath and bed - the other says goodnight after In the Night Garden. If he sees us both in his bath he wants us both to get him to sleep. Sure, he cries a bit for DH but he's with his Daddy and he's not distressed crying, just tired and eczema pain crying (the moisturiser stings!).

WRT the teddy, DS picked his comfort toy aged 1 year. Sure, it was a toy that had been in his cot before, but he wasn't fussed about Herr Hare before then. Now he wakes in a blind panic if he can't find the bunny. He has 3 different cries: the first is "I'm awake and nearly asleep... I'm off again" (sometimes we have to stand at his doorway for him to drift off), the second is "I'm awake and need a bit of help to go back to sleep because I'm the wrong temperature/getting teeth/eczema stings" and that's about 5 minutes, the third is "WHERE IS MY BUNNY? THE WORLD IS ENDING! FIND THE BUNNY!" (There's also the "I'm up for the day and bored of playing alone" cry but that's different from a night cry.)

As for "not settle" for Dad - make sure Dad is doing all the right things! DH and I now have different ways of settling DS but at first it was "he won't do it for me" ie "I can't be bothered to learn how to do it and don't like getting up at night or giving up my free time." A bit of crying with his dad won't kill him - Daddy loves his son and can care for him, your DS will soon realise that. Maybe more things together in the day would help that attachment form.