Thanks for the replies ladies. I think the A time between last nap and bedtime seems to be okay. I think possibly SA might be the problem combined with maybe needing a longer wind down. I have been doing wi/wo with him and it is working but he still fusses a lot and cries but I keep reassuring him and he is finally able to settle himself most of the time. Tonight was not too good though. He had a late nap this afternoon until 4pm so I aimed for an 8pm bedtime. We did our routine and wind down and he did some fussing but then some playing. He seemed to be not tired at all. He played for almost 40 minutes then started fussing again. Of course he's also at the age where he throws his blanky out of the crib and then cries the instant it hits the floor.
He was finally starting to settle at 9pm but that's when his sister had to go to bed (they share a room and she had a nap today too therefore a late bedtime for her... that's another story!
) Once we took DD into the room to tuck her in DS shot right up again from his mattress and started to fuss and cry again. In the end we gave him a second bottle of milk and he drank it all and fell asleep drinking it... which is a rare thing since we've always put him to bed awake. He is definitely showing signs of SA though these past couple of weeks so perhaps that is most of the problem right there. I will continue the wi/wo with him as it does seem to be working most nights. I just miss how it was before where I'd tuck him in and he'd roll over and snuggle his blanky and go to sleep. I hate hearing him cry. He's been an angel baby from the start so I guess I was spoiled!
Anyway, I had to LOL about the 1 year molars. The poor little guy doesn't have one tooth yet. That perhaps is another thing that might be going on. He is ready to cut his first tooth. I can see the white bump just heaping on his little gum but it has not split the skin yet. I bet it is bothering him too. I have tried some Tylenol a few nights and it seemed to help. I'm sure it's a combination of things but I'm glad to know that his A time seems okay. Thanks so much for the help. I will keep trying to help him settle with wi/wo and I think I'll start to add some books to his wind down as well. DD was having book time before bed long before 12 months so I think it is high time we start with DS! Thanks again.