Ok might try an earlier W2S - I had the same thoughts as you re: waking up good for the day. I only thought W2S worked if you did it an hour before they are due to wake up. Do I wake him up completely, or just make him stir?
Having a toy in there means that he plays in his cot, so I am torn as to what I should do? I can see how he can be UT when I put him to bed, but then become OT due to playing with his toy. But I don't want to put him to bed even earlier, just so he can have a plaay and fall asleep at a reasonable hour? Arghh.
If he wakes up early (like today), I will try and put him down earlier? If he wakes around 6.15-6.30, I normally have him in bed by 12-12.30. I don't let him take a toy for his day sleeps, but it still takes him a while to fall asleep. I haven't looked for tired signs for a long time.. Also, he goes to daycare, and they get him to sleep at 12pm (he is always the last to go to sleep, and she pats his back which I don't do because he would want to play), but she said that when there are other children asleep, it almost prompts them to go to sleep too.
He had transitioned properly by 13 months, so yes, quite young. He would do anywhere from 1.5 hours to 3 hours, but I could never see a trend?